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UNITED STATESSECURITIES AND EXCHANGE COMMISSION

Washington, D.C. 20549____________________________________________________________

Form 20-F___________________________________________________________

☐ REGISTRATION STATEMENT PURSUANT TO SECTION 12(b) OR 12(g) OF THE SECURITIES EXCHANGE ACT OF 1934

OR☒ ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934

For the fiscal year ended December 31, 2020OR

☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934

OR☐ SHELL COMPANY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934

Commission file number 001-31909

ASPEN INSURANCE HOLDINGS LIMITED(Exact name of registrant as specified in its charter)

Bermuda(Jurisdiction of incorporation or organization)

141 Front Street, Hamilton, HM19, Bermuda(Address of principal executive offices)

MarkCloutierExecutiveChairmanandChiefExecutiveOfficer

141FrontStreet,Hamilton,HM19,BermudaTelephone:+1441-295-8201,Email:mark.cloutier@aspen.co(Name,Telephone,E-mailand/orFacsimileNumberandAddressofCompanyContactPerson)

Securities registered pursuant to Section 12(b) of the Act:Title of Each Class Trading Symbol Name of Each Exchange on Which Registered

5.95%Fixed-to-FloatingRatePerpetualNon-CumulativePreferenceShares AHLPRC NewYorkStockExchange5.625%PerpetualNon-CumulativePreferenceShares AHLPRD NewYorkStockExchangeDepositaryShares,eachrepresentinga1/1000thinterestinashareof5.625%PerpetualNon-CumulativePreferenceShares AHLPRE NewYorkStockExchange

Securities registered pursuant to Section 12(g) of the Act: None.Securities for which there is a reporting obligation pursuant to Section 15(d) of the Act: None.

Indicatethenumberofoutstandingsharesofeachoftheissuer’sclassesofcapitalorcommonstockasofthecloseoftheperiodcoveredbytheannualreport:60,395,839ordinaryshares.Indicatebycheckmarkiftheregistrantisawell-knownseasonedissuer,asdefinedinRule405oftheSecuritiesAct.Yes☐No☒Ifthisreportisanannualortransitionreport,indicatebycheckmarkiftheregistrantisnotrequiredtofilereportspursuanttoSection13orSection15(d)oftheAct:Yes☐No☒Indicatebycheckmarkwhethertheregistrant(1)hasfiledallreportsrequiredtobefiledbySection13or15(d)oftheExchangeActof1934duringthepreceding12months(orforsuch

shorterperiodsthattheregistrantwasrequiredtofilesuchreports),and(2)hasbeensubjecttosuchfilingrequirementsforthepast90days.YesýNo☐IndicatebycheckmarkwhethertheregistranthassubmittedelectronicallyeveryInteractiveDataFilerequiredtobesubmittedpursuanttoRule405ofRegulationS-T(§232.405ofthis

chapter)duringthepreceding12months(orforsuchshorterperiodthattheregistrantwasrequiredtosubmitsuchfiles).Yes☒No☐Indicatebycheckmarkwhethertheregistrantisalargeacceleratedfiler,anacceleratedfiler,anon-acceleratedfiler,asmallerreportingcompanyoranemerginggrowthcompany.Seethe

definitionsof“largeacceleratedfiler,”“acceleratedfiler,”“smallerreportingcompany”and“emerginggrowthcompany”inRule12b-2oftheExchangeAct.:

Largeacceleratedfiler ☐ Acceleratedfiler ☐ Non-acceleratedfiler ☒ Smallerreportingcompany ☐ Emerginggrowthcompany ☐

IfanemerginggrowthcompanythatpreparesitsfinancialstatementsinaccordancewithU.S.GAAP,indicatebycheckmarkiftheregistranthaselectednottousetheextendedtransitionperiodforcomplyingwithanyneworrevisedfinancialaccountingstandardsprovidedpursuanttoSection13(a)oftheExchangeAct.☐

Indicatebycheckmarkwhichbasisofaccountingtheregistranthasusedtopreparethefinancialstatementsincludedinthisfiling:

U.S.GAAP ☒ InternationalFinancialReportingStandardsasissuedbytheInternationalAccountingStandardsBoard ☐ Other ☐

Ifthisisanannualreport,indicatebycheckmarkwhethertheregistrantisashellcompany(asdefinedinRule12b-2oftheAct).Yes☐No☒

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ASPEN INSURANCE HOLDINGS LIMITEDFORM 20-F

TABLE OF CONTENTS

PageExplanatoryNote 2

PART IItem1. IdentityofDirectors,SeniorManagementandAdvisors 3Item2. OfferStatisticsandExpectedTimetable 3Item3. KeyInformation 3Item4. InformationontheCompany 31Item4A. UnresolvedStaffComments 56Item5. OperatingandFinancialReviewandProspects 57Item6. Directors,SeniorManagementandEmployees 95Item7. MajorShareholdersandRelatedPartyTransactions 101Item8. FinancialInformation 101Item9. TheOfferandListing 102Item10. AdditionalInformation 102Item11. QuantitativeandQualitativeDisclosuresaboutMarketRisk 110Item12. DescriptionofSecuritiesOtherthanEquitySecurities 112

PART IIItem13. Defaults,DividendArrearagesandDelinquencies 112Item14. MaterialModificationstotheRightsofSecurityHoldersandUseofProceeds 112Item15. ControlsandProcedures 112Item16A. AuditCommitteeFinancialExpert 113Item16B. CodeofEthics 113Item16C. PrincipalAccountantFeesandServices 113Item16D. ExemptionsfromtheListingStandardsforAuditCommittees 114Item16E. PurchasesofEquitySecuritiesbytheIssuerandAffiliatedPurchasers 114Item16F. ChangeinRegistrant’sCertifyingAccount 114Item16G. CorporateGovernance 114Item16H. MineSafetyDisclosure 115

PART IIIItem17. FinancialStatements 115Item18. FinancialStatements 1Item19. Exhibits i

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EXPLANATORY NOTEReferences in this Annual Report on Form 20-F (this “report”) to the “Company,” the “Aspen Group,” “we,” “us” or “our” refer to Aspen Insurance

Holdings Limited (“Aspen Holdings”) or Aspen Holdings and its consolidated subsidiaries, as the context requires. References to “Aspen Holdings” mean onlyAspen Insurance Holdings Limited. Our principal operating subsidiaries are: Aspen Insurance U.K. Limited (“Aspen U.K.”), Aspen Bermuda Limited (“AspenBermuda”), Aspen Specialty Insurance Company (“Aspen Specialty”), Aspen American Insurance Company (“AAIC”) and Aspen Underwriting Limited (“AUL”)(as corporate member of our Lloyd’s operations, which are managed by Aspen Management Agency Limited “AMAL”), each referred to herein an “OperatingSubsidiary” and collectively referred to as the “Operating Subsidiaries”). References to “Aspen Capital Markets” means business conducted by our subsidiariesthat participate in alternative reinsurance markets, including Peregrine Reinsurance Ltd (“Peregrine”), Silverton Re Ltd. (“Silverton”), Aspen Cat Fund Limited(“ACF”) and related management entities, including Aspen Capital Advisors Inc. (“Aspen Advisors”) and Aspen Capital Management, Ltd (“ACM”).

References in this report to “U.S. Dollars,” “dollars,” “$” or “¢” are to the lawful currency of the United States of America, references to “British Pounds,”“pounds,” “GBP” or “£” are to the lawful currency of the United Kingdom and references to “euros” or “€” are to the lawful currency adopted by certainmember states of the European Union (the “E.U.”), unless the context otherwise requires.

OnFebruary15,2019,theCompanycompleteditsmergerwithHighlandsMergerSub,Ltd.(“MergerSub”),awhollyownedsubsidiaryofHighlandsBermudaHoldco, Ltd. (formerly known as Highlands Holdings, Ltd.) (“Parent”). Merger Sub merged with and into the Company (the “Merger”), with the CompanycontinuingasthesurvivingcompanyandasawhollyownedsubsidiaryofParent.Parent,aBermudaexemptedcompany,isanaffiliateofcertaininvestmentfundsmanagedbyaffiliatesofApolloGlobalManagement,Inc.,aleadingglobalinvestmentmanager(collectivelywithitssubsidiaries,“Apollo”).

As a result of the Merger, all of the Company’s publicly traded ordinary shares were automatically canceled. The ordinary shares of the Company ceasedtradingontheNewYorkStockExchange(“NYSE”)priortotheopeningoftradingonFebruary15,2019.TheCompany’spreferencesharesanddepositarysharescontinuetobelistedontheNYSEunderthefollowingsymbols:AHLPRC,AHLPRDandAHLPRE.

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PART I

Item 1. Identity of Directors, Senior Management and Advisors

Notapplicable.

Item 2. Offer Statistics and Expected Timetable

Notapplicable.

Item 3. Key Information

A. Selected Financial Data

Thefollowingtablesetsforthourselectedhistoricalfinancialinformationfortheperiodsendedandasofthedatesindicated.Youshouldreadthefollowingselectedconsolidatedfinancialinformationinconjunctionwithotherinformationcontainedinthisreport,includingtheauditedconsolidatedfinancialstatementsandrelatednotesinItem18and“OperatingandFinancialReviewandProspects”inItem5ofthisreport.

Twelve Months Ended December 31, 2020 2019 2018 2017 2016 ($ in millions, except per share amounts and percentages)Summary Income Statement Data Grosswrittenpremiums $ 3,703.6 $ 3,442.4 $ 3,446.9 $ 3,360.9 $ 3,147.0Netpremiumswritten 2,582.9 2,427.9 2,082.0 2,212.5 2,593.7Netpremiumsearned 2,532.6 2,293.3 2,214.7 2,306.6 2,637.3Lossandlossadjustmentexpenses (1,840.8) (1,679.7) (1,573.0) (1,994.7) (1,576.1)Amortizationofdeferredpolicyacquisitioncosts,general,administrativeandcorporateexpenses (876.6) (934.3) (863.3) (902.7) (1,019.0)

Netinvestmentincome 154.6 197.3 198.2 189.0 187.1(Loss)incomefromoperationsbeforeincometax (31.5) (218.8) (156.0) (281.8) 209.5Net(loss)incomeafterincometax (40.1) (241.7) (145.8) (266.4) 203.4Basicweightedaveragesharesoutstanding(millions) 60.9 60.9 59.7 59.8 60.5Summary Balance Sheet Data Totalcashandinvestments $ 7,502.6 $ 7,801.9 $ 7,823.1 $ 8,687.8 $ 9,174.1Premiumsreceivable 1,377.8 1,403.4 1,551.1 1,596.3 1,472.5Totalassets 13,185.4 12,580.5 12,532.9 12,906.4 12,090.1Lossandlossadjustmentexpensereserves 7,165.3 6,951.8 7,074.2 6,749.5 5,319.9Reservesforgrossunearnedpremiums 1,817.4 1,737.7 1,709.1 1,820.8 1,618.6Loannotesissuedbyvariableinterestentities,atfairvalue — — 4.6 86.6 223.4Long-termdebt 299.9 299.8 424.7 549.5 549.3Totalshareholders’equity 2,997.6 2,725.5 2,640.4 2,912.9 3,648.3

______________ Total cash and investments include cash, cash equivalents, fixed income securities, equities, bank loans, other investments, short-term investments and

catastrophebonds.Premiumsreceivableincludingfundswithheld.Includingcashwithinconsolidatedvariableinterestentitiesof$69.9millionasatDecember31,2020(2019—$69.1million;2018—$26.9million;2017—

$166.6million;2016—$291.3million).Alloftheloannotesissuedbyourconsolidatedvariableinterestentities,atfairvalue,wereclassifiedascurrentliabilitiesdueandpayableinlessthanone

year.Formoreinformation,refertoItem18,Note5,“VariableInterestEntities.”AsattheyearendedDecember31,2019,reinsurancepremiumspayablesandretainedearningswererestatedby$15.6millionfromJanuary1,2017onwards

toaccountforadditionalcededpremiumsonexcessoflosscededreinsurancecontracts.

(1,3)

(2)

(4)

(5)

(1)

(2)

(3)

(4)

(5)

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OnFebruary15,2019,ParentacquiredalloftheCompany’sordinaryshares.Asaresult,alloftheCompany’spreviouslypubliclytradedordinaryshareswereautomaticallycanceledandceasedtradingontheNYSE.Accordingly,persharedataisnolongerrequiredtobepresentedbytheCompany.RefertoItem18,Note1,“History,OrganizationandBusinessCombination”foradditionaldetailsoftheMerger.

B. Capitalization and Indebtedness

Notapplicable.

C. Reasons for the Offer and Use of Proceeds.

Notapplicable.

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D. Risk Factors

You should carefully consider the following risk factors and all other information set forth in this report, including our consolidated financial statements andthe notes thereto. Any of the risks described below could materially and adversely affect our business, operating results or financial condition. The risk factorsdescribed below could also cause our actual results to differ materially from those in the forward-looking and other statements contained in this report and otherdocuments that we file with the SEC. The risks and uncertainties described below are not the only ones we face. However, these are the risks we believe to bematerial as of the date of this report. Additional risks not presently known to us or that we currently deem immaterial may also impair our future business,financial condition or operating results.

Introduction

Aswithanypubliclytradedcompany,investinginourpreferencesharesandothersecuritiescarriesrisks.Ourriskmanagementstrategyisdesignedtoidentify,measure,monitorandmanagematerialrisksthatwecancontrolandwhichcouldadverselyaffectourfinancialconditionandoperatingresults.Wehaveinvestedsignificantresourcestodeveloptheappropriateriskmanagementpoliciesandprocedurestoimplementthisstrategy.Nonetheless,thefuturebusinessenvironmentis intrinsically uncertain and difficult to forecast and, as a result, our risk management methods may not be successful. For more information on our riskmanagementstrategy,refertoItem4,“BusinessOverview-RiskManagement-RiskManagementStrategy.”

Risks Relating to Recent Developments

The coronavirus pandemic and the responses thereto have already adversely affected our business and operations, and the ultimate effects thereof on ourbusiness, our operations and our financial condition and results of operations remain highly uncertain and impossible to predict.

TheglobalspreadofCOVID-19,andthegovernmentalandregulatoryactionstakentomitigatetheireffects,haveledtosignificantandongoingeconomicandsocietaldisruption,includingsignificantmarketvolatility.ThelevelofCOVID-19infectionscontinuestoriseincertaincountriesandthethreatofnewoutbreaksandnewstrainsofthevirusstilllooms.Manyofthedirectandindirecteffectsresultingfromsuchoutbreaksarestillactiveordevelopingand,assuch,itisnotpossibleatthistimetoprovideadefinitiveestimateofpotentialinsurance,reinsuranceorinvestmentexposuresoranyotherdirectorindirecteffectstheCOVID-19crisismayhaveonourresultsofoperations,financialconditionorliquidity.

WewereadverselyaffectedbytheCOVID-19crisisduringthe2020financialyear.Refertothedisclosureundertheheading“OperatingandFinancialReviewandProspects”inItem5ofthisreportformoreinformation.ThefullextentofourlossesfromtheCOVID-19pandemicwillultimatelydependonitsseverityanddurationandsuchlossescouldhaveamaterialadverseeffectonourresultsofoperations,financialconditionorliquidity.Wehaveidentifiedexposuresarisingfromourunderwritingofinsurancepoliciesinouraccident&healthline,whichwestartedtowinddowninMarch2020,aswellasourongoingproperty,marine&energyandcasualtylines. Inourreinsurancebusinesswehaveidentifiedexposuresarisingfromourcontingency(event cancellation), propertyandcasualtylines.TheseexposuresandpotentialexposuresincludedirectclaimsrelatingtoCOVID-19(e.g.lossesformedicalcarerelatedtoCOVID-19oreventcancellationlosses) and indirect exposures arising from the emerging financial distress the COVID-19 crisis is causing. We note that other lines may be affected as thepandemicandassociatedeconomicdownturndevelopandasnewinformationisdiscovered.

Our exposures are controlled and limited by our insurance and reinsurance contracts, which include specific terms and conditions defining if and howourpoliciesrespondtolossesarisingfromtheCOVID-19pandemic.However,legislative,regulatoryorjudicialactions(e.g.theUKFinancialConductAuthoritytestcase on business interruption insurance and subsequent legal actions, including appeals) and social influences which may seek to extend coverage or paymenttermsbeyondintendedcontractualobligationsorresultinanincreaseinthefrequencyorseverityofclaimsbeyondexpectedlevels.Thereareongoinglawsuitsandotherlegalactionschallengingthepromptnessofcoveragedeterminationsorthecoveragedeterminationsthemselvesonclaimsunderapplicableinsuranceorreinsurancepolicies,including,amongothers,businessinterruptionclaims,whichcouldresultinincreasedclaims,litigationandrelatedexpenses.Itisnotpossibleto predict when or how litigation related to the COVID-19 crisis and coverage disputes will be finally resolved, which further impairs our ability to estimatepotentialinsuranceorreinsuranceexposure.

A number of State legislatures in the United States are considering legislation to retroactively change existing primary insurance coverage for businessinterruption and loss of use to cover coronavirus related losses, and other jurisdictions may do the same. Many States have, to date, either mandated insurersprovidegraceperiodsforthepaymentofpremiumsorrequestedinsurersprovidesuchgraceperiodsintheeventaninsuredrequestsapaymentdeferral, whichcould,ifprolonged,adverselyaffectcashflows.SomeStateshaveissuedregulatoryguidanceencouragingpremiumrelieforareturnof

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premiumstocedantsandclients.Ifanysuchguidanceweretobecomemandatory,thiscouldhaveamaterialadverseeffectonourresultsofoperationsandcashflows.Inaddition,anumberofproposalshavebeenintroducedorproposedtoalterthefinancingofpandemic-relatedriskinseveralofthemarketsinwhichweoperate.

Certainofourpolicyholdersandintermediariesmaynotpaypremiumsowedtousduetoinsolvencyorotherreasons.Insolvency,liquidityproblems,distressedfinancial condition due to the impact of the COVID-19 pandemic or the general effects of economic recession may increase the risk that policyholders orintermediaries, such as insurance brokers, may not pay a part of or the full amount of premiums owedto us, despite an obligation to do so. The terms of ourcontracts,oractionsbyourregulators,maynotpermitustocancelourinsuranceeventhoughwehavenotreceivedpayment.Wemayfurtherdecide(orbeobligedbyregulation)torefundpremiumsalreadypaidwhereitisjudgedthattheCOVID-19pandemichasreducedthecustomerneedforinsurance.Ifrefundsornon-paymentsbecomewidespread,whetherasaresultofinsolvency,lackofliquidity,adverseeconomicconditions,operationalfailureorotherwise,itcouldhaveamaterialadverseimpactonourrevenuesandresultsofoperations.

Wesetourreservesbasedonourbestinterpretationofthecurrentlegalpositioninapplicablejurisdictions,buttheselegislative,regulatory,judicialactionsandsocialinfluencesmakeitdifficulttopredictthetotalamountoflosseswecouldincurasaresultofthepandemic.

Inaddition,financialmarketvolatilitycouldadverselyaffectourinvestmentresultsoraccesstothecapitalmarkets.Whileourinvestmentportfoliocomprisesprimarilygovernmentandotherfixedincomesecurities,andwearenotsignificantlyexposedtoequitymarkets,ourcorporatebondportfoliocouldbesubjecttodefault riskin theevent of extendeddisruptionto trade, andour strategic asset allocationincludes middle market loans(“MML”), commercial mortgageloans(“CML”)andothermortgageloanarrangementsthatmaybeadverselyaffectedbytheCOVID-19crisis.

WealsofaceoperationalrisksasaresultoftheCOVID-19crisis.Wehavetransitionedtoaworkfromhomemodelformostemployeesand,asaresult,thereisariskthatbusinessoperationswillbedisrupteddueto,cybersecurityattacksordatasecurityincidents,higherthananticipatedwebtrafficandcallvolumesaswellaslackofsufficientbroadbandinternetconnectivityforemployeesandthirdpartiesworkingfromhome,amongotherthings.Inaddition,illnessessufferedbykeyemployees could prevent or delay the performance of critical business and financial reporting functions; widespread illnesses suffered by our employees mayrenderusunabletoperformnormalbusinessfunctionsandoperateourbusinessonaday-to-daybasis.

We rely on vendors, including some located overseas, for a number of services. As the COVID-19 crisis has had a global impact, our vendors could alsoexperiencedisruptionstotheiroperationsandwhilewehavecontingencyplansforsomelevelofdisruption,therecanbenoassurancethatissueswiththebusinessoperationsofourvendorswouldnothaveamaterialeffectonourownoperations.

Further,wecannotpredictatthistimehowtheCOVID-19crisiswillimpactdemandforourinsuranceandreinsuranceproductsinthefuture.Whileweexpectdemandfor(re)insurancemay,asaresultoftheCOVID-19crisis,increaseinsomelinesofbusiness,anddecreaseinothers,thefutureimpactoftheCOVID-19crisisonourindustryandourbusinesswilldependonarangeoffactors,includingthedurationofmitigationeffortsandtheavailabilityofvaccinesand/orotheralternativetreatmentsolutions,theseverityoftheimpactofmitigationeffortsonbusinessesandbusinessactivity,thescopeandefficacyofgovernmentalstimulusand other relief efforts, the extent to which legislative or regulatory efforts or court cases succeed in shifting some of the burden of the pandemic to insurers(particularly for business interruption) on a retroactive basis, and the severity and duration of, and the speed of recovery from, recessionary impacts. OurdisclosuresshouldbereadinthecontextoftheevolvingCOVID-19crisisandtherelateduncertainties,whetherornotspecificreferenceismadethereto.

Inaddition,theCOVID-19pandemicmayhavetheeffectoftriggeringorintensifyingmanyoftherisksdescribedelsewhereunderthisItem3D.RiskFactors.

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Risks Related to Our Business

(Re)insurance Risks

Our financial condition and operating results may be adversely affected by the occurrence of natural and man-made disasters.

Aspartofourinsuranceandreinsuranceoperations,weassumesubstantialexposuretolossesresultingfromnaturaldisasters,man-madecatastrophesandothercatastropheevents.Catastrophescanbecausedbyvariousunpredictableevents,including,butnotlimitedto,tropicalstorms,cyclones,hurricanes,winterstorms,tornadoes,hailstorms,floods,explosions,wildfires,drought,pandemicdisease,volcaniceruptions,earthquakesandtsunamis.Catastrophescanalsobeman-madesuchasactsofwar,actsofterrorismandotherintentionallydestructiveacts,includingthoseinvolvingnuclear,biological,chemicalorradiologicalevents,cyber-attacks,explosions,infrastructurefailuresandlossesresultingfrompoliticalinstability, governmentactionthatishostiletocommercial interestsandsovereign,sub-sovereignandcorporatedefaults.

Theincidence,severityandmagnitudeofcatastrophesareinherentlyunpredictableandourlossesfromsuchcatastropheshavebeenandcanbesubstantial.Inaddition,weexpectthatincreasesinthevaluesandconcentrationsofinsuredpropertywillincreasetheseverityofsuchoccurrencesinthefutureandthatglobalclimate change may increase the frequency and severity of severe weather events, wildfires and flooding. Similarly, changes in global political and economicconditionsmayincreaseboththefrequencyandseverityofman-madecatastropheeventsinthefuture.Althoughweattempttomanageourexposuretosucheventsthrough a multitude of approaches (including geographic diversification, geographic limits, individual policy limits, exclusions or limitations from coverage,purchaseofreinsuranceandexpansionofsupportivecollateralizedcapacity),theavailabilityofthesemanagementtoolsmaybedependentonmarketfactorsand,totheextentavailable,maynotrespondinthewaythatweexpect.Inaddition,asinglecatastrophiceventcouldaffectmultiplegeographiczonesorthefrequencyorseverityofcatastrophiceventscouldexceedourestimates.Asaresult,theoccurrenceofoneormorecatastrophiceventsoranunusualfrequencyofsmallereventsmayresultinsubstantialvolatilityin,andmaymateriallyadverselyaffect,ourbusiness,financialconditionoroperatingresults.

Withregardtocyber-attacks, thisisanareawherethethreatlandscapeisevolving,andthereisariskthatincreasesinthefrequencyandseverityofcyber-attacksonourpolicyholderscouldadverselyaffectourfinancialconditionandoperatingresults.Thisriskisalsodependentonourpolicyholders’cybersecuritydefenses,andourissuanceofpolicytermswhichrespondtotheevolvingthreatlandscape.Inaddition,ourexposuretocyber-attacksincludesexposuretosilentcyberrisks, meaningrisksandpotential lossesassociatedwithpolicieswherecyberriskisnotspecificallyincludednorexcludedinthepolicies. Evenincaseswhereweattempttoexcludelossesfromcyber-relatedrisks,therecanbenoassurancethatacourtorarbitrationpanelwillinterpretpolicylanguage,orotherwiseissuearuling,favorabletous.

Global climate change may have a material adverse effect on our operating results and financial condition if we do not adequately assess and price forany increased frequency and severity of catastrophes resulting from these environmental factors.

Thereiswidespreadconsensusinthescientificcommunitythatthereisalong-termupwardtrendinglobalairandseatemperatureswhichislikelytoincreasethe severity and frequency of severe weather events over the coming decades. Rising sea levels are also expected to add to the risks associated with coastalfloodingin manygeographical areas. Largescale climate changecouldalsoincrease boththefrequencyandseverity of natural catastrophes andour loss costsassociatedwithpropertydamageandbusinessinterruptionduetostorms,floodsandotherweather-relatedevents.Inaddition,globalclimatechangecouldimpairourabilitytopredictthecostsassociatedwithfutureweathereventsandcouldalsogiverisetonewenvironmentalliabilityclaimsintheenergy,manufacturingandotherindustriesweserve.

Given the scientific uncertainty of predicting the effect of climate cycles and climate change on the frequency and severity of catastrophes and the lack ofadequatepredictivetools,wemaynotbeabletoadequatelymodeltheassociatedexposuresandpotentiallossesinconnectionwithsuchcatastropheswhichcouldhaveamaterialadverseeffectonourbusiness,financialconditionoroperatingresults.

We could face unanticipated losses from war, terrorism and political unrest, government action that is hostile to commercial interests and from sovereign,sub-sovereign and corporate defaults, and these or other unanticipated losses could have a material adverse effect on our financial condition or operatingresults.

Wehavesubstantialexposuretounexpected,largelossesresultingfromman-madecatastrophiceventssuchas,butnotlimitedto,actsofwar,actsofterrorismandlossesresultingfrompoliticalinstability,governmentactionthatishostiletocommercialinterestsandsovereign,sub-sovereignandcorporatedefaults.Theserisksareinherentlyunpredictableasitis

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difficulttopredicttheiroccurrencewithstatisticalcertaintyortoestimatetheamountoflosssuchanoccurrencemaygenerate.TerroristattacksaroundtheglobeandongoingunrestintheMiddleEastandNorthKoreahavehighlightedtheunpredictablebutincreasinglypresentthreatofterrorismandpoliticalinstability.

Terrorist eventscouldgenerategreater interest inpolitical violenceinsurancecoverageandgreaterawarenessoftherisksmultinational corporationsfaceinconflict-proneregions.Wecloselymonitortheamountandtypesofcoverageweprovideforterrorismriskunderinsurancepoliciesandreinsurancetreaties.Evenincaseswherewehavedeliberatelysoughttoexcludesuchcoverage,therecanbenoassurancethatacourtorarbitrationpanelwillinterpretpolicylanguageorissuearulingfavorabletous.Accordingly,wemaynotbeabletoeliminateourexposuretoterroristeventsandthereremainsariskthatourreserveswillnotbeadequatetocoversuchlossesshouldtheymaterialize.Notably,theTerrorismRiskInsuranceProgramReauthorizationActof2019(the“TRIAReauthorization”)doesnotprovidecoverageforreinsurancelosses.Inaddition,wehavelimitedterrorismcoverageforexposuretocatastrophelossesrelatedtoactsofterrorisminthereinsurancethat wepurchase. AlthoughtheTRIAReauthorizationprovidesbenefits intheevent of certainacts of terrorismoccurringintheUnitedStates,thosebenefitsaresubjecttoadeductibleandotherlimitations.

Ourcreditandpoliticalriskinsurancelineofbusinessprotectsinsuredswithinterestsinforeignjurisdictionsintheeventgovernmentalactionpreventsthemfromexercisingtheircontractualrightsandmayalsoprotecttheirassetsagainstphysicaldamageperils.Theinsuranceprovidedmayincludecoverforlossarisingfrom expropriation, forced abandonment, license cancellation, trade embargo, contract frustration, non-payment, war on land or political violence (includingterrorism,revolution,insurrectionandcivilunrest).

Ourcreditandpoliticalrisklineofbusinessalsoprovidesnon-paymentcoverageonspecificloanobligations.Weinsuresovereignnon-paymentandcorporatenon-payment as a result of commercial as well as political riskevents. Thevast majority of thecorporate non-payment credit insuranceprovidedis for single-namedilliquidrisks,primarilyintheformofseniorbankloansthatcanbeindividuallyanalyzedandunderwritten.Wealsoavoidtermsinourcreditinsurancecontractswhichintroduceliquidityrisk,mostnotably,intheformofacollateralizationrequirementuponaratingsdowngrade.Wealsoattempttomanageourexposure,byamongotherthings,settingcreditlimitsbycountry,region,industryandindividualcounterpartyandregularlyreviewingouraggregateexposures.However, due to globalization, political instability in one region can spread to other regions. Geopolitical uncertainty regarding a variety of domestic andinternationalmatters,suchastheU.S.politicalandregulatoryenvironment,thepotentialfordefaultbyoneormoreEuropeansovereigndebtissuersandtheexitofthe United Kingdom from the E.U. single market and customs union (“Brexit”) could have a material adverse effect on our results of operations or financialcondition.

The effects of emerging claim and coverage issues in our business are uncertain.

Asindustrypracticesandlegislative,regulatory,judicial,social,financial,technologicalandotherenvironmentalconditionschange,unexpectedandunintendedissuesrelatedtoclaimsandcoveragemayemerge.Theseissuesmayadverselyaffectourbusinessbyeitherextendingcoveragebeyondourunderwritingintentorbyincreasingthefrequencyandseverityofclaims.Insomeinstances,thesechangesmaynotbecomeapparentuntilafterwehaveissuedinsuranceorreinsurancecontractsthatareaffectedbythechanges.Asaresult,thefullextentofliabilityunderourinsuranceorreinsurancecontractsmaynotbeknownformanyyearsafterissuance.

OneemergingriskcurrentlyfacingthepropertyandcasualtyindustryistheopioidcrisisintheUnitedStates.Numerouslawsuitshavebeenfiledonbehalfofstates, countiesandmunicipalitiesallegingavarietyofclaimsandseekingcompensatoryandotherdamagescausedbytheopioidcrisis. Ingeneral, defendantsnamedintheselawsuitshavebeenmajorpharmaceuticalcompanies,wholesaledistributors,retailpharmaciesanddoctors.Sincetheselawsuitsareinearlystages,and taking into consideration higher verdicts and settlements that have been emerging, particularly against corporate defendants in respect of casualty claims(knownas“socialinflation”)intheUnitedStates,weareunabletopredicttheoutcomeoftheselawsuitsortheirpotentialimpacttoourfinancialresults.

Inaddition,theeffectoftheCOVID-19outbreakonthepropertyandcasualtyindustryisnotyetknown.See“RisksrelatingtoRecentDevelopments—Thecoronaviruspandemicandtheresponsetheretohavealreadyadverselyaffectedourbusinessandoperations,andtheultimateeffectsthereofonourbusiness,ouroperationsandourfinancialconditionandresultsofoperationsremainhighlyuncertainandimpossibletopredict.”

The (re)insurance business is historically cyclical and we expect to experience periods with excess underwriting capacity and unfavorable premium ratesand policy terms and conditions.

The insurance and reinsurance industry has historically been cyclical. It is characterized by periods of intense competition on price and policy terms andconditionsduetoexcessiveunderwritingcapacity(a“soft”market)andperiodswhen

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shortagesofcapacitypermitfavorablepremiumlevels(a“hard”market).Anincreaseinpremiumratesisoftenoffsetbyanincreasingsupplyofinsuranceandreinsurancecapacity,viacapitalprovidedbynewentrants,newcapitalmarketinstrumentsandstructuresand/orthecommitmentofadditionalcapitalbyexistinginsurersandreinsurers,whichmaycausepricestodecrease.Anyofthesefactorscouldleadtoasignificantreductioninpremiumrates,lessfavorablepolicytermsandconditionsandfewersubmissionsforourunderwritingservices.Inaddition,changesinthefrequencyandseverityoflossessufferedbyinsuredsandinsurersmayalsosignificantly affect the cycles of the (re)insurance business as couldchanges in economic, legal, political andsocial factors. If wefail to managethecyclicalnatureofthe(re)insurancebusiness,ouroperatingresultsandfinancialconditioncouldbemateriallyadverselyaffected.

A material proportion of our business relies on the assessment and pricing of individual risks by third parties.

Weauthorizemanaginggeneralagents,generalagentsandotherproducerstowritebusinessonourbehalffromtimetotimewithinunderwritingauthoritiesweprescribe. We rely on the underwriting controls of these agents and producers to write business within the underwriting authorities we provide. Although wemonitorourunderwritingonanongoingbasis,ourmonitoringeffortsmaynotbeadequateandouragentsandproducersmayexceedtheirunderwritingauthoritiesorotherwisebreachobligationsowedtous.Thereisalsotheriskthatwemaybeheldresponsibleforobligationsthatarisefromtheactsoromissionsofthirdpartiesiftheyaredeemedtohaveactedonourbehalf.Inaddition,ouragents,producers,insuredsorotherthirdpartiesmaycommitfraudorotherwisebreachtheirobligationto us. Tothe extent that our agents, producers, insureds or other third parties exceedtheir authorities, commit fraudor otherwise breachobligationsowedtous,ouroperatingresultsandfinancialconditionmaybemateriallyadverselyaffected.

Ourrelianceonthird-partyassessmentandpricingofindividualriskextendstoourreinsurancetreatybusiness.Similartootherreinsurers,wedonotseparatelyevaluateeachoftheindividualrisksassumedundermostreinsurancetreaties.Wearethereforelargelydependentontheoriginalunderwritingdecisionsmadebycedingcompanies.Wearesubjecttotheriskthatthecedingcompaniesmaynothaveadequatelyevaluatedtheriskstobereinsuredandthatthepremiumscededtousmaynotadequatelycompensateusfortherisksweassumeandthelosseswemayincur.Asaresultofthisrelianceoncedingcompanies,ouroperatingresultsandfinancialconditionmaybemateriallyadverselyaffected.

The failure of any risk management and loss limitation methods we employ could have a material adverse effect on our financial condition and operatingresults.

Weemploy various risk management and loss limitation methods. Weseek to manage our loss exposure by maintaining disciplined underwriting processesdesignedtoguidethepricing,termsandacceptanceofrisk.Theseprocesses,whichmayincludetheuseofpricingmodels,areintendedtoensurethatpremiumsreceivedaresufficienttocovertheexpectedlevelsofattritionallossesandacontributiontothecostofcatastrophesandlargelosses,wherenecessary.Wealsoseektomitigateourlossexposurebywritinganumberofourinsuranceandreinsurancecontractsonanexcessoflossbasis,suchthatweonlypaylossesthatexceedaspecifiedretention.Wealsoseektolimitcertainrisks,suchascatastrophesandpoliticalrisks,bygeographicdiversification.Geographiczonelimitationsinvolvesignificantunderwritingjudgments,includingthedeterminationofzoneboundariesandtheallocationofpolicylimitstozones.Inthecaseofproportional(alsoknownasprorata)propertyreinsurancetreaties,weoftenseekperoccurrencelimitationsorlossandlossexpenseratiocapstolimittheimpactoflossesfromany one event, although we may not be able to obtain such limits in certain markets. Various provisions in our policies intended to limit our risks, such aslimitationsorexclusionsfromcertaincoverageandchoiceofforum,maynotalwaysbeenforceable.Purchasingreinsuranceisanotherlosslimitationmethodweemploywhichmaynotalwaysrespondinthewayintendedduetodisputesrelatingtocoverageterms,exclusionsorcounterpartycreditrisk.

Thereareinherentlimitationsinalloftheseactionsanditispossiblethataneventorseriesofeventscouldresultinlosslevelsthatcouldhaveanadverseeffecton our financial condition and results of operations. It is also possible that our controls and monitoring efforts may be ineffective, permitting one or moreunderwriterstoexceedtheirunderwritingauthorityandcauseusto(re)insurerisksoutsidetheagreeduponguidelinesorthatlossescouldmanifestthemselvesinways that we do not anticipate and that our risk mitigation strategies are not designed to address. Additionally, various provisions in our policies, such aslimitationsorexclusionsfromcoverageorchoiceofforumnegotiatedtolimitourriskmaynotbeenforceableinthemannerweintend.Asaresult,oneormorenaturalcatastrophesand/orterrorismorothereventscouldresultinclaimsthatsubstantiallyexceedourexpectations,whichcouldhaveamaterialadverseeffectonourfinancialconditionoroperatingresults.

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The reinsurance that we purchase may not always be available on favorable terms or we may choose to retain a higher proportion of particular riskscompared to previous years.

Fromtimetotime,marketconditionshavelimited,andinsomecasesprevented,insurersandreinsurersfromobtainingthetypesandamountsofreinsurancethattheyconsideradequatefortheirbusinessneeds.Accordingly,wemaynotbeabletoobtainourdesiredamountofreinsuranceorretrocessionprotectionontermsthatareacceptabletousfromentitieswithasatisfactorycreditratingorwhichiscollateralized.Evenifsuchcapacityisavailable,wemayalsochoosetoretainahigherproportionofparticularrisksthaninpreviousyearsduetopricing,termsandconditionsorstrategicemphasis.Wemayalsoseekalternativemeansoftransferringrisk,includingexpandedparticipationviaourAspenCapitalMarketsplatforminalternativereinsurancestructures.Thesesolutionsmaynotprovidecommensurate levels of protectioncomparedtotraditional retrocession. Ourinability toobtainadequate reinsuranceorother protectionfor our ownaccount atfavorablepricesandonacceptabletermscouldhaveamaterialadverseeffectonourbusiness,operatingresultsandfinancialcondition.

Our financial condition and operating results may be adversely affected if actual claims exceed our loss reserves.

Ouroperatingresultsandfinancialconditiondependonourabilitytoaccuratelyassessthepotentiallossesassociatedwiththerisksthatwe(re)insure.Whilewebelieve that our loss reserves as of December 31, 2020 are adequate, establishing an appropriate level of loss reserves is an inherently uncertain process andrequiresaconsiderableamountofjudgment.Therearemanyfactorsthatwouldcauseourreservestoincreaseordecrease,whichinclude,butarenotlimitedto,changes in claim severity, changes in the expected level of reported claims, judicial action changing the scope and/or liability of coverage, changes in thelegislative,regulatory,socialandeconomicenvironmentandunexpectedchangesinlossinflation.Inaddition,changesinthelevelofinflationalsoresultinanincreasedlevelofuncertaintyinourestimationoflossreserves,particularlyforthoselinesofbusinessthatareconsidered“long-tail,”suchascasualty,astheyrequire a relatively longperiod of timeto finalize andsettle claims for a givenaccident year. Tothe extent actual claims exceed our expectations, wewill berequired to recognize the less favorable experience immediately which could cause a material increase in our provisions for liabilities and a reduction in ourprofitability,includingoperatinglossesandreductionofcapital.

Wecannot estimate losses fromwidespreadcatastrophic events, suchas hurricanes andearthquakes, usingtraditional actuarial methods. Themagnitudeandcomplexityoflossesassociatedwithcertainoftheseeventsinherentlyincreasethelevelofuncertaintyand,therefore,thelevelofmanagementjudgmentinvolvedin arriving at loss reserve estimates. Similarly, our estimate of ultimate losses related to the COVID-19 pandemic is subject to significant uncertainty. ThisuncertaintyisdrivenbytheinherentdifficultyinmakingassumptionsaroundtheimpactoftheCOVID-19pandemicduetothelackofcomparableevents, theongoing nature of the event, and its far-reaching impacts to world-wide economies and the health of the global population.Asa result, actual losses for theseeventsmayultimatelydiffermateriallyfromcurrentestimates.

While we believe that our earliest accident years are capable of providing us with meaningful actuarial indications, estimates and judgments for new(re)insurancelinesofbusinessaremoredifficulttomakethanthosemadeformorematurelinesofbusinessbecausewehavemorelimitedhistoricalinformationthroughDecember31,2020.Asignificantportionofourcurrentlossreservesisinrespectofincurredbutnotreported(“IBNR”)reserves.ThisIBNRreserveisbasedalmostentirelyonestimatesinvolvingactuarialandstatisticalprojectionsofourexpectationsoftheultimatesettlementandadministrationcosts.Inadditionto limited historical information for certain lines of business, we utilize actuarial models as well as historical insurance industry loss development patterns toestablishlossreserves.Accordingly,actualclaimsandclaimexpensespaidmaydeviate,perhapssubstantially,fromourreserveestimates,whichcouldmateriallyadverselyaffectourfinancialresults.

Only reserves applicable to losses incurred up to the reporting date may be set aside in our financial statements, with no allowance for future losses. Ourestimatesofreservesforlossesandlossexpensesalsoincludeassumptionsaboutfuturepaymentsforsettlementofclaimsandclaims-handlingexpenses,suchasmedicaltreatmentandlitigationcosts.WewritecasualtybusinessintheUnitedStates,theUnitedKingdom,Australiaandcertainotherterritorieswhereclaimsinflation has in many years run at higher rates than general inflation. To the extent economic or social inflation causes these costs to increase above reservesestablished for these claims, we will be required to increase our loss reserves with a corresponding reduction in our net income in the period in which thedeficiencyisidentified,whichcouldmateriallyadverselyaffectourfinancialresults.

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Market and Liquidity Risks

Our investments are subject to interest rate, credit, and real estate related risks, which may adversely affect our net income and may adversely affect theadequacy of our capital.

Weinvestthenetpremiumswereceiveunless,oruntil suchtimeas,wepayoutlossesand/oruntil theyaremadeavailablefordistributiontoordinaryandpreferredshareholders,topayinterestonorredemptionofdebtandpreferredshares,orotherwiseusedforgeneralcorporatepurposes.Investmentresultscomprisea substantial portion of our income. We, accordingly, are exposed to significant financial and capital market risks, including changes in interest rates, creditspreads,andrealestateprices,foreignexchangerates,marketvolatility,theperformanceoftheeconomyingeneral,andotherfactorsoutsideourcontrol.

Interestratesarehighlysensitivetomanyfactors,includingfiscalandmonetarypoliciesofmajoreconomies,inflation,economicandpoliticalconditionsandotherfactorsoutsideourcontrol.Changesininterestratescannegativelyaffectnetinvestmentincomeinthat,inadeclininginterestrateenvironment,investmentsinfixedmaturitiesandshort-terminvestments(fixedmaturityportfolio)wouldearninterest incomeatlowerrates. Inadeclininginterest rateenvironment, themarket value of our fixed incomeportfolio would increase; however, in a rising interest rate environment, the market value of our fixed incomeportfolio willdecline. Dependingonourliquidityneedsandinvestment strategy, wemayliquidate investments prior tomaturityat alossinordertocoverliabilities astheybecomedueortoinvestinotherinvestmentopportunitiesthathavebetterexpectedlongertermprofitability.

Ourfixedmaturityportfolioisprimarilyinvestedinhighquality,investmentgradesecurities,includingcollateralizedloanobligations(“CLOs”).However,weinvestaportionoftheportfolioinsecuritiesthatarebelowinvestmentgrade.Wealsoinvestaportionofourportfolioinotherinvestmentssuchasunratedprivatefixedandfloatingrateinvestments,andotherspecialtyassetclasses.Thesesecuritiesgenerallypayahigherrateofinterestorreturnandmayhaveahigherdegreeofcreditordefaultrisk.Thesesecuritiesmayalsobelessliquidintimesofeconomicweaknessormarketdisruptions.

Inaddition,weinvestdirectlyandindirectlyinprivateloansandrealestateassets,which,asdescribedmorefullybelow,aresubjecttoadditionalrisks.

Changes in the method for determining the London Interbank Offered Rate (“LIBOR”) and the potential replacement of LIBOR may affect our costof capital and net investment income.

TheFCAhasannounceditsdesiretophaseouttheuseofLIBORbytheendof2021,whichmayaffectinvestmentsandborrowings.WhenLIBORceasestoexist,wemayneedtorenegotiatethetermsofcertainofourinvestmentsorourcreditfacilitieswhichutilizeLIBORasafactorindeterminingtheinterestrate,includingpossiblytoreplaceLIBORwiththenewstandardthatisestablished.TheU.S.FederalReservehasalsobegunpublishingaSecuredOvernightFundingRate which is intended to replace U.S. dollar LIBOR. Plans for alternative reference rates for other currencies have also been announced. It is not possible topredicthowinvestmentandcreditmarketswillrespondtothesenewrates,andtheeffectthatanychangesinLIBORorthediscontinuationofLIBORmighthaveonneworexistingfinancialinstruments,includingtheeffectivenessorineffectivenessofhedges,however,suchchangesmayadverselyimpactthevalueofourinvestmentsandourcostofsuchformsofcapital.

OnNovember18,2020,IntercontinentalExchange,Inc.(ICE),ownerofICEBenchmarkAdministrationLimited(IBA),publishedanannouncementthatIBAwill consult on its intention to cease the publication of all GBP, EUR, CHF, and JPY LIBOR settings. On November 30, 2020, ICE published a similarannouncementwithrespecttoUSDLIBOR.Inparticular,ICEannouncedthatIBAwillconsultonitsintentiontoceasethepublicationoftheone-weekandtwo-monthUSDLIBORsettingsimmediatelyfollowingtheLIBORpublicationonDecember31,2021andtoceasetheremainingUSDLIBORsettingsimmediatelyfollowingtheLIBORpublicationonJune30,2023.

Potentialchanges,oruncertaintyrelatedtosuchpotentialchanges,mayadverselyaffectthemarketforsecuritiesreferencingLIBOR,whichinturncouldhavean adverse effect on our LIBOR-linked investments as well as our credit facilities, such as the letter of credit facilities with commercial lenders. In addition,changesorreformstothedeterminationorsupervisionofLIBORmayresultinasuddenorprolongedincreaseordecreaseinreportedLIBOR,whichcouldhaveanadverseimpactonthemarketforLIBOR-basedsecuritiesorcostofcapital.

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Our investments in private, secured CMLs and private, secured MMLs are subject to credit risk, market risk, servicing risk, loss from catastrophicevents and other risks, which could diminish the value that we obtain from such investments.

Asof December 31, 2020, a small portion of our total invested assets were invested in private, secured CMLsand in private, secured MMLs. Defaults byborrowersinthepaymentorperformanceoftheirobligationsunderlyingtheseassetscouldreduceourinvestmentincomeandrealizedinvestmentgainsorresultintherecognitionofinvestmentlosses.Forexample,thevalueofourrealestate-relatedassetsdependsinpartonthefinancialconditionoftheborrowers,thevalueoftherealpropertiesunderlyingthemortgagesand,forcommercialproperties,thefinancialconditionofthetenantsofthepropertiesunderlyingthosemortgages,aswellasgeneralandspecificeconomictrendsaffectingtheoveralldefaultrate.Anunexpectedlyhighrateofdefaultoncommercialmortgagesand/ormiddlemarketloansmaylimitsubstantiallytheabilityoftheissuerofsuchsecuritiestomakepaymentstotheloanholders,reducingthevalueofthosesecurities.

TheCMLandMMLportfoliosthatwehold,facebothdefaultanddelinquencyrisk.AnincreaseinthedelinquencyordefaultrateofourCML/MMLportfoliosorgeographicorsectorconcentrationwithinourCML/MMLportfolioscouldmateriallyandadverselyimpactourfinancial conditionandresults ofoperations.Anyfailure to managetheseriskseffectively couldmaterially andadversely affect our financial conditionandresults of operations. In general, anysignificantweaknessinthebroadermacroeconomyorsignificantproblemsinaparticularrealestatemarketorcorporatemarketmaycauseadeclineinthevalueoftherealestatemarketandcorporateassetssecuringtheloansinthatmarket,therebyincreasingtheriskofdelinquency,defaultandforeclosure.Thiscould,inturn,haveamaterialadverseeffectonourcreditlossexperience.

FormoreinformationonourCMLandMMLinvestments,whichwealsorefertoas“privately-heldinvestments,”refertoItem18,Note4ofourconsolidatedfinancialstatements,“Investments.”

A portion of our invested assets are relatively illiquid and we may fail to realize profits from these assets for a considerable period of time, or lose some orall of the principal amount we invest in these assets if we are required to sell our invested assets at a loss at inopportune times to meet our insurance,reinsurance or other obligations.

Weseektoconfigureourinvestmentportfoliotoprovideandmaintainsufficientliquiditytosupportourinsurance,reinsuranceandotherobligations.However,in order to provide necessary long-termreturns and to achieve our strategic goals, at times a portion of our assets may be relatively illiquid. Aportion of ourinvestmentsareinsecuritiesthatarenotpubliclytradedorthatotherwiselackliquidity,suchasourprivately-heldfixedmaturityandfloatingratesecurities,belowinvestmentgradesecurities,andalternativeinvestments.

Werecordourrelativelyilliquidtypesofinvestmentsatfairvalue.Ifwewereforcedtosellcertainofourassets,therecanbenoassurancethatwewouldbeabletosellthemforthevaluesatwhichsuchassetsarerecordedandwemightbeforcedtosellthematsignificantlylowerprices.Whenweholdasecurityorposition,it isvulnerabletopriceandvaluefluctuationsandmayexperiencelossesifweareunabletosellorhedgetheposition.Thus,it maybeimpossibleorcostlyforustoliquidatepositionsrapidlyinordertomeetunexpectedobligations.Thispotentialmismatchbetweentheliquidityofourassetsandliabilitiescouldhaveamaterialandadverseeffectonourbusiness,financialcondition,resultsofoperationsandcashflows.

WealsoinvestinCLOsandcontrolovertheCLOsinwhichweinvestisexercisedthroughcollateral managers, whomaytakeactionsthatcouldadverselyaffectourinterests,andwemaynothavetherighttodirectcollateralmanagement.TheremayalsobelessinformationavailabletousregardingtheunderlyingdebtinstrumentsheldbyCLOsthanifwehadinvesteddirectlyinthedebtoftheunderlyingcompanies.OurinvestmentsinCLOsarealsosubjecttoliquidityriskasthereisalessliquidmarketforCLOs.Accordingly,wemaysufferunrealizeddepreciationandcouldincurrealizedlossesinconnectionwiththesaleofourCLOinvestments.

Volatility and uncertainty in general economic conditions and in financial and mortgage markets could adversely impact our business prospects,operating results, financial position and liquidity.

In recent years, and in recent months due to the COVID-19 outbreak, global financial markets have been characterized by volatility and uncertainty.Unfavorable economicconditionscouldincrease our fundingcosts, limit our access tothecapital markets or makecredit harder toobtain. Uncertainties inthefinancialandmortgagemarketsmayalsoaffectourcounterpartieswhichcouldadverselyaffecttheirabilitytomeettheirobligationstous.

Deterioration or volatility in the financial markets or general economic and political conditions could result in a prolonged economic downturn or triggeranotherrecessionandouroperatingresults,financialpositionandliquiditycouldbemateriallyandadverselyaffected.Further,unfavorableeconomicconditionscouldhaveamaterialadverseeffecton

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certainofthelinesofbusinesswewrite,including,butnotlimitedto,creditandpoliticalrisks,professionalliabilityandsuretyrisks.

Weprovidecreditreinsurancetomortgageguarantyinsurersandcommercialcreditinsurers.Weareexposedtotheriskthatlossesfrommortgageinsurancematerially exceed the net premiums that are received to cover such risks, which may, subject to liability caps, result in operating and economic losses to us.Mortgageinsuranceunderwritinglossesthathavethepotentialtoexceedourriskappetiteareassociatedwiththesystemicimpactsofseveremortgagedefaults,drivenbylargescaleeconomicdownturnsandhighunemployment.

The determination of the amount of allowances and impairments taken on our investments is highly subjective and could materially impact our operatingresults or financial position.

Weperformadetailedanalysiseachreportingperiodendtoassessdeclinesinthefairvaluesofavailableforsaledebtsecuritiesinaccordancewithapplicableaccountingguidanceregardingtherecognitionandpresentationofcurrentexpectedlosses.Theprocessofdetermininganallowanceforavailableforsalesecuritiesrequiresjudgmentandinvolvesanalyzingmanyfactors.Foradditionalinformationregardingthisprocess,andthechangestotheapplicableaccountingpolicies,refertoItem18,Note2(c)ofourconsolidatedfinancialstatements,“BasisofPreparationandSignificantAccountingPolicies—AccountingforInvestments,CashandCashEquivalents.”,andItem18,Note2(c)ofourconsolidatedfinancialstatements,“BasisofPreparationandSignificantAccountingPolicies—AccountingPronouncements.”Assessingtheaccuracyoftheallowancesreflected,inourfinancialstatementsisinherentlyuncertaingiventhesubjectivenatureoftheprocess.Furthermore,additionalimpairmentsmayneedtobetakenorallowancesprovidedinthefuturewithrespecttoeventsthatmayimpactspecificinvestments.Whileour current allowance is not material, the current allowance may not be indicative of future impairments or allowances. Thus, future material impairmentsthemselvesoranyerrorinaccuratelyaccountingforthemmayhaveamaterialadverseeffectonourfinancialconditionorresultsofoperations.

Our financial condition or operating results may be adversely affected by currency fluctuations that we may not be effective at mitigating.

OurreportingcurrencyistheU.S.dollar,however,asignificantportionofouroperationsisconductedoutsidetheUnitedStatesinavarietyofforeign(non-U.S.)currencies.Accordingly,wearesubjecttolegal,economicandmarketrisksassociatedwithdevaluationsandfluctuationsincurrencyexchangerates.Ourassets and liabilities denominated in foreign currencies are therefore exposed to changes in currency exchange rates, which may be material. The principalcurrenciescreatingforeignexchangeriskaretheBritishPounds,theEuro,theSwissFranc,theAustralianDollar,theCanadianDollarandtheSingaporeDollar.AtDecember31,2020,approximately14.7%ofgrosswrittenpremiumsweredenominatedinnon-U.S.currencies.Weemployvariousstrategies,includingtheuseofforeignexchangeforwardcontracts andotherderivativefinancial instruments, tomanageourexposuretoforeigncurrencyexchangerisk. Totheextent thattheseexposuresarenotfullyoffset orhedged, orthehedgesareineffectiveat mitigatingadverseeffects, ourfinancial results andconditionmaybenegativelyimpactedbyfluctuationsinforeigncurrencyexchangerates.SovereigndebtconcernsinEuropeandrelatedfinancialrestructuringefforts,whichmaycausethevalue of the Euro to deteriorate, and Brexit, which caused significant volatility in currency exchange rates, especially between the U.S. dollar and the Britishpound,maymagnifytheserisks.

Credit Risks

Our operating results may be adversely affected by the failure of policyholders, brokers or other intermediaries or reinsurers to honor their paymentobligations.

Inaccordancewithindustrypractice,wegenerallypayamountsowedonclaimsunderourinsuranceandreinsurancecontractstobrokersandthesebrokers,inturn, pay these amounts to the policyholders that purchased insurance and reinsurance from us. In some jurisdictions where we write a significant amount ofbusiness,ifabrokerfailstomakesuchapaymentitishighlylikelythatwewillbeliabletothepolicyholderforthedeficiencybecauseoflocallawsorcontractualobligations.Likewise,whenthepolicyholderpayspremiumsforpoliciestobrokersforpaymenttous,thesepremiumsaregenerallyconsideredtohavebeenpaidand,inmostcases,thepolicyholderwillnolongerbeliabletousforthoseamountswhetherornotwehaveactuallyreceivedthepremiums.Consequently,weassumeadegreeofcreditriskassociatedwithbrokerswithrespecttomostofour(re)insurancebusiness.

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Inaddition,bankruptcy,liquidityproblems,distressedfinancialconditionsorthegeneraleffectsofeconomicrecessionmayincreasetheriskthatpolicyholdersmaynotpayapartof,orthefullamountof,premiumsowedtousdespiteanobligationtodoso.Thetermsofourcontractsorlocallawmaynotpermitustocancel our insurance evenif wehavenot received payment. If non-payment becomes widespread, whether as a result of bankruptcy, lack of liquidity, adverseeconomicconditions,operationalfailure,delayduetolitigation,badfaithandfraudorotherevents,itcouldhaveamaterialadverseimpactonourbusinessandoperatingresults.

Wepurchasereinsuranceforourownaccountinordertomitigatetheeffectofcertainlargeandmultiplelossesuponourfinancialcondition.Ourreinsurersorcapitalmarketcounterpartsaredependentontheirratingsinordertocontinuetowritebusinessandsomehavesuffereddowngradesinratingsinthepastasaresultoftheirexposures.Ourreinsurersorcapitalmarketcounterpartiesmayalsobeaffectedbyadversedevelopmentsinthefinancialmarkets,whichcouldadverselyaffect their ability to meet their obligations to us. Insolvency of these counterparties, their inability to continue to write business or reluctance to make timelypaymentsunderthetermsoftheiragreementswithuscouldhaveamaterialadverseeffectonusbecauseweremainliabletoourinsuredsorcedantsinrespectofthereinsuredrisks.

Duringperiodsofeconomicuncertainty,suchasthecurrentenvironment,ourconsolidatedcreditrisktothesepartiesmaymateriallyincrease.

Strategic Risks

Our business may be adversely affected if third-party outsourced service providers fail to satisfactorily perform certain technology and business processfunctions.

Weoutsourcecertaintechnologyandbusinessprocessfunctionstothirdpartiesincludingoffshoreandcloudserviceprovidersandmayincreasinglydosointhefuture.Ifwedonoteffectivelydevelop,implementandmonitorouroutsourcingstrategy,third-partyprovidersdonotperformasanticipatedorweexperiencetechnologicalorotherproblemswithatransition,wemaynotrealizeproductivityimprovementsorcostefficienciesandmayexperienceoperationaldifficulties,increased costs and loss of business. Our outsourcing of certain technology and business processes functions to third parties may expose us to enhanced risksrelatedtodatasecurity, whichcouldresult inmonetaryandreputational damages. Inaddition,ourabilitytoreceiveservicesfromthird-partyprovidersmaybeimpacted bycultural differences, political instability, unanticipated regulatory requirements or policies. Asa result, our ability to conduct our business maybeadverselyaffected.

Competition and consolidation in the (re)insurance industry could reduce our growth and profitability.

Insuranceandreinsurancemarketsarehighlycompetitive.WecompeteonaninternationalandregionalbasiswithmajorU.S.,Bermuda,Europeanandotherinternational(re)insurersandunderwritingsyndicates,includingLloyd's,someofwhichhavegreaterfinancial,marketingandmanagementresourcesthanwedo.We also compete with new companies that continue to be formed to enter the (re)insurance markets. In addition, capital market participants have createdalternativeproductsthatareintendedtocompetewithreinsuranceproducts.Untilrecently,newandalternativecapitalinflowsinthe(re)insurancemarketandtheretentionbycedantsofmorebusinesshadcausedanexcesssupplyof(re)insurancecapital,andmayagaininthefuture.Wehavesoughttoaddressthisriskbydevelopingourowncapitalmarketscapabilitybutthereisnoguaranteeitwillsucceed.

Therehasalsobeenalargevolumeofmergerandacquisitionactivityinthe(re)insurancesectorinrecentyearswhichmaycontinueandwemayexperienceincreased competition as a result of that consolidation with consolidated entities having enhanced market power. As the (re)insurance industry consolidates,competitionforcustomerswillbecomemoreintenseandtheimportanceofacquiringandproperlyservicingeachcustomerwillbecomegreater.

Increased competition could result in fewer submissions, lower premium rates, less favorable policy terms and conditions and greater expenses relating tocustomeracquisitionandretention,whichcouldhaveamaterialadverseimpactonouroperatingresultsorfinancialcondition.

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Our Operating Subsidiaries are rated and our Lloyd’s business benefits from a rating by one or more of A.M. Best and S&P and a decline in any of theseratings could adversely affect our standing among brokers and customers and cause our premiums and earnings to decrease.

Ratings have become an increasingly important factor in establishing the competitive position of insurance and reinsurance companies. Rating agenciesrepresentindependentopinionsofthefinancialstrengthofinsurersandreinsurersandtheirabilitytomeetpolicyholderobligations.TheratingsofourOperatingSubsidiariesaresubjecttoperiodicreviewby,andmaybeplacedoncreditwatch,reviseddownwardorrevokedatthesolediscretionof,A.M.BestorS&P.RefertoItem4,“BusinessOverview-Ratings.”Theseratingsareintendedtomeasureacompany’sabilitytorepayitsobligationsandarebaseduponcriteriaestablishedbytheratingagencies.Ratingsmaybesolicitedorunsolicited.

The rating agencies with whom we maintain an interactive rating relationship for the purposes of the solicited ratings, currently A.M. Best and S&P,continuouslyevaluateustoconfirmthatwecontinuetomeetthecriteriaoftheratingassignedtous.Ourratingsmaybereviseddownwardorrevokedatthesolediscretionoftheratingagencies.Thefinancialstrengthratingsassignedbyratingagenciestoinsuranceorreinsurancecompaniesarebaseduponfactorsrelevanttocedants, whichincludefactorsnotentirelywithinourcontrol, includingfactorsimpactingthefinancial services, insuranceandreinsuranceindustriesgenerally.Financialstrengthratingsbyratingagenciesarenotratingsofsecuritiesorrecommendationstobuy,holdorsellanysecurity.

If our Operating Subsidiaries’ or if Lloyd’s ratings are reduced from their current levels by either A.M. Best or S&P, our competitive position in the(re)insurance industry might suffer and it may be more difficult for us to market our products, expand our (re)insurance portfolio and renew our existing(re)insurancepoliciesandagreements. Aratingdowngrademayalsorequireustoestablishtrustsorpostlettersofcredit forcedingcompanyclientsandcouldtriggerprovisionsallowingsomeclients toterminate their (re)insurancecontracts withus. Somecontracts alsoprovideforthereturnofpremiumtothecedingclientintheeventofaratingdowngrade.Itisincreasinglycommonforourreinsurancecontractstocontainsuchterms.Whetheracedantwouldexerciseanyofthese rights could depend on various factors, such as the reason for and the extent of such downgrade, the prevailing market conditions and the pricing andavailability of replacement reinsurance coverage. A downgrade could result in a substantial loss of business as ceding companies and brokers that place suchbusinessmovetootherreinsurerswithhigherratingsandthereforesuchdowngrademaymateriallyandadverselyimpactourbusiness,operatingresults,liquidityandfinancialflexibility.

In addition, a downgrade of the financial strength rating of Aspen U.K., Aspen Bermuda, AAIC or Aspen Specialty by A.M. Best below “B++” wouldconstitute an event of default under our revolving credit facility. Additionally, the cost and availability of unsecured financing are generally dependent on theborrower’s long-term and short-term debt ratings. A lower rating may lead to higher borrowing costs, thereby adversely impacting our liquidity and financialflexibilityandbyextensionourbusiness,financialconditionandresultsofoperations.

We have experienced a ratings downgrade and there can be no assurance that we and our subsidiaries will not experience any further downgrades, whichmay result in an adverse effect on our business, financial condition and operating results.

Asnotedabove,ratingswithrespecttoclaimspayingabilityandfinancialstrengthhavebecomeincreasinglyimportantfactorsinestablishingthecompetitivepositionofinsuranceandreinsurancecompaniesandwillalsoimpactthecostandavailabilityofcapitaltoaninsurancecompany.OurexistingratingsbyA.M.BestandS&Prepresentanimportantconsiderationinmaintainingcustomerconfidenceinusandinourabilitytomarketinsuranceproducts.Ratingorganizationsregularlyanalyzethefinancialperformanceandconditionofinsurers.

OnMarch26,2020,S&PdowngradedthefinancialstrengthandissuercreditratingsofAspenBermudaandAspenU.K.to“A-”(Strong)from“A”(Strong).The long term issuer credit rating of Aspen Holdings was downgraded to “BBB” from “BBB+”. The outlook assigned to all these ratings is stable. Our U.S.Operatingsubsidiaries, AAICandAspenSpecialty,arenotcurrentlyratedbyS&Pandhaveafinancial strengthratingof“A”(Excellent) byA.M.Bestwithanegative outlook. OnApril 1, 2020, A.M.Best affirmedthe financial strength rating of “A”(Excellent) for AspenBermuda, AspenU.K. AspenSpecialty andAAICbutreviseditsoutlooktonegativefromstable.OurLloyd’soperationsbenefitfromtheLloyd’smarketfinancialstrengthratingof“A”(Excellent)withastableoutlookbyA.M.Bestand“A+”(Strong)withastableoutlookbyS&P.

In addition, as a result of their rating of Highlands Holdings Bond Issuer, Ltd. and Highlands Holdings Bond Co-Issuer, Inc. (the “Issuers”) and the $500million aggregate principal amount of their 7.625% / 8.375% Senior Secured PIK Toggle Notes due 2025 (the “Notes”), S&P will, going forward, take intoconsideration the Issuers in their view of the wider Aspen Group when evaluating the adequacy of our capital reserves for purposes of determining financialstrengthandissuercreditratingsaccordedtoourOperatingSubsidiaries.Inaddition,S&Pexpectsustomaintaincapitaladequacyabovethe“AAA”

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leveltomaintainour“A-”rating.Shouldweexperienceweakerthan-expectedunderwritingperformance,shouldourcapitaladequacypositiondeclineandremainbelowthe“AAA”levelforaprolongedperiod,shouldourfinancialleveragemateriallyincreaseorliquiditymateriallydecrease,amongotherfactors,wemayberequired to maintain a greater amount of capital in order to maintain our existing ratings or becomesubject to a ratings downgrade. Our capital adequacywasabovethe“AAA”levelasatDecember31,2020andisabovethe“AAA”levelasofthedateofthisfiling.

BothA.M.Best andS&Parewidelyrecognizedinsurancecompanyratingagenciesandsomepolicyholders arerequiredtoobtaininsurancecoveragefrominsurance companies that havean“A-”(Strong) ratingor higher. BecauseA.M.Best andS&Pcontinually monitor companies with regardto their ratings, ourratingscouldchangeat anytime. Anydowngradeinour ratingsmayimpair our ability tosell insurancepolicies andcouldmaterially andadverselyaffect ourcompetitivepositionintheinsuranceindustry,futurefinancialconditionandoperatingresults.

Any future acquisitions, growth of our operations through the addition of new lines of (re)insurance business, expansion into new geographic regionsand/or joint ventures or partnerships may expose us to risks.

Aspartofourlong-termstrategy,wehavepursued,andmaycontinuetopursue,growththroughacquisitionsand/orstrategicinvestmentsinnewbusinessesorenteringintostrategicventureswiththirdparties.Thenegotiationofthesetransactionsaswellastheintegrationofanacquiredbusinessornewpersonnelcouldresultinasubstantialdiversionofmanagementresources.Successfulintegrationdepends,amongotherthings,onourabilitytoeffectivelyintegrateacquiredbusinessesornewpersonnelintoourexistingriskmanagementandfinancialandoperationalreportingsystems,establishsatisfactorybudgetaryandotherfinancialcontrols,manageanyregulatoryissuescreatedbyourentryintonewmarketsandgeographiclocations,retainkeypersonnelandobtainpersonnelrequiredforexpandedoperations.Thefailuretointegratesuccessfullyortomanagethechallengespresentedbytheintegrationprocessmayhaveanadverseeffectonourbusiness,financialconditionorresultsofoperations.

Therecanbenoassurancethattheintegrationofacquiredbusinessesornewpersonnelwillbesuccessful,thatwewillrealizeanticipatedsynergies,costsavingsandoperationalefficiencies,orthatthebusinessacquiredwillprovetobeprofitableorsustainable.Thefailuretointegrateacquiredbusinessessuccessfullyortomanagethechallengespresentedbytheintegrationprocessmayadverselyimpactourfinancialresults.Acquisitionscouldinvolvenumerousadditionalriskssuchaspotentiallossesfromunanticipatedlitigationorlevelsofclaimsandinabilitytogeneratesufficientrevenuetooffsetacquisitioncosts.Inaddition,thevalueofassetsacquiredmaybelowerthanexpectedormaydiminishduetocreditdefaultsorchangesininterestratesortheliabilitiesassumedmaybegreaterthanexpected.Ourabilitytogrowthroughacquisitionswilldepend,inpart,onoursuccessinaddressingtheserisks.Ourfailuretomanagesuccessfullyanyoftheforegoingchallengesandrisksmayadverselyimpactourresultsofoperations.

We depend on a few brokers for a large portion of our insurance and reinsurance revenues and the loss of business provided by any one of those brokerscould adversely affect us.

Wemarket our (re)insurance worldwide primarily through (re)insurance brokers and derive a significant portion of our business froma limited number ofbrokers.RefertoItem4,“BusinessOverview-BusinessDistribution”belowforourprincipalbrokersbysegment.Ourrelationshipswithourbrokersandagentsare based onthe quality of our underwriting and claimservices, as well as our financial strength ratings. Anydeterioration in these factors could result in thebrokersadvisingourclientstoplacetheirbusinesswithother(re)insurers.Inaddition,thesebrokersandagentsalsohave,ormayinthefutureacquire,ownershipinterestsininsuranceandreinsurancecompaniesthatmaycompetewithusandthesebrokersmayfavortheirown(re)insurersoverothercompanies.Lossofallorasubstantialportionofthebusinessprovidedbyoneormoreofthesebrokerscouldhaveamaterialadverseimpactonourbusinessandresultsofoperations.

Inaddition,therehasbeenatrendofincreasedconsolidationofagentsandbrokersandofagentsandbrokersreducingthenumbersofinsurerswithwhichtheydobusinesstogainefficiencyfortheirplacementefforts.Aswedistributemostofourproductsthroughagentsandbrokers,consolidationcouldimpactourabilityto access business and our relationships with, and fees paid to, agents and brokers. In the Lloyds’s market, independent London wholesalers continue to beacquiredbylargerglobalbrokers,whichmayresultinenhancedmarketpowerfortheselargerbrokersinplacing(re)insurance.Consolidationofdistributorsmayalsoincreasethelikelihoodthatdistributorswilltrytorenegotiatethetermsofexistingsellingagreementstotermslessfavorabletous.Asbrokersmergewithoracquireeachother,anyresultingfailureorinabilityofbrokerstomarketourproductssuccessfully,orthelossofasubstantialportionofthebusinesssourcedbyoneormoreofourkeybrokers,couldhaveamaterialadverseeffectonourbusinessandresultsofoperations.

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We are exposed to risks in connection with our management of alternative reinsurance platforms on behalf of investors in any entities Aspen CapitalMarkets manages or could manage in the future.

Those of our subsidiaries that are engaged in the management of alternative reinsurance platforms as part of our Aspen Capital Markets division mayowecertain legal duties andobligations to third-party investors (including reporting obligations) andare subject to a variety of often complex lawsandregulationsrelatingtothemanagementofthosestructures.Althoughwecontinuallymonitorourpoliciesandprocedurestoensurecompliance,faultyjudgments,simpleerrorsormistakes,orthefailureofourpersonneltoadheretoestablishedpoliciesandprocedurescouldresultinourfailuretocomplywithapplicablelawsorregulationswhichcouldresultinsignificantliabilities,penaltiesorotherlossesandsignificantlyharmourbusinessandresultsofoperations.

Inaddition,ourthird-partyinvestorsmaydecidenottorenewtheirinterestsintheentitieswemanage,whichcouldmateriallyimpactthefinancialconditionofsuchentities.Certainofourthird-partycapitalinvestorsprovidesignificantcapitalinvestmentinrespectoftheentitieswemanage.Thelossoralterationofthiscapitalsupportcouldbedetrimentaltoourfinancialconditionandresultsofoperations.Moreover,wecanprovidenoassurancethatwemaybeabletoattractandraiseadditionalthird-partycapitalforourexistingmanagedentitiesorforpotentialnewmanagedentitiesandthereforewemayforegoexistingand/orpotentialattractivefeeincomeandotherincome-generatingopportunities.

Furthermore, notwithstanding any capital holdback, we may decide to return to our investors all or a portion of the third-party capital held by entities wemanageascollateralpriortothematurityspecifiedinthetermsoftheparticularunderlyingtransactionaldocuments.Areturnofcapitaltoourinvestorsisfinal.Asaresult,ifwereleasecollateralearlyandcapitalisreturnedtoourinvestors,wemaynothavesufficientcollateraltopaytheclaimsassociatedwithsuchlossesintheeventlossesaresignificantlylargerthanweanticipated.

We may require additional capital in the future, which may not be available or may only be available on unfavorable terms.

Ourfuturecapitalrequirementsdependonmanyfactors,includingourabilitytowritenewbusinesssuccessfully,deploycapitalintomoreprofitablebusinesslines,identifyacquisitionopportunities,manageinvestmentsandpreservecapitalinvolatilemarkets,andestablishpremiumratesandreservesatlevelssufficienttocoverlosses.Totheextentourfundsareinsufficienttofundfutureoperatingrequirementsorcoverclaimslosses,wemayneedtoraiseadditionalfundsthroughcorporatefinancetransactionsorcurtailourgrowthandreduceourliabilities.Anysuchfinancing,ifavailableatall,maybeontermsthatarenotfavorabletous.Ourabilitytoraisesuchcapital successfullywoulddependuponthefacts andcircumstancesat thetime, includingourfinancial positionandoperatingresults,market conditions and applicable regulatory filings and legal issues. If we cannot obtain adequate capital on favorable terms, or obtain it at all, our business,financialconditionandoperatingresultscouldbeadverselyaffected.

Our debt, credit and International Swaps and Derivatives Association (“ISDA”) agreements may limit our financial and operational flexibility, whichmay affect our financial condition, liquidity and ability to conduct our business.

Wehaveincurredindebtednessandmayincuradditionalindebtednessinthefuture.Additionally,wehaveenteredintocreditfacilitieswithvariousinstitutionswhichproviderevolvinglinesofcredittousandourOperatingSubsidiariesandissuelettersofcredittoourclientsintheordinarycourseofbusiness.WehavealsoenteredintoISDAagreementsrelatingtoderivativetransactions.RefertoItem18,Note8ofourconsolidatedfinancialstatements,“DerivativeContracts”forinformationontheinterestrateswapsweexecutedinJanuary2019.During2020,weunwoundtheremaining$1,800.0millionofourinterestrateswaps.Wemayreplace these swaps in the future as we remain vigilant to interest rate developments that arise from the COVID-19 induced economic crisis and considerdefensivelypositioningtheportfolioifwarranted.

The agreements relating to our debt, credit facilities and our ISDAagreements contain covenants that may limit our ability, among other things, to borrowmoney,makeparticulartypesofinvestmentsorotherrestrictedpayments,sellassets,mergeorconsolidate.Someoftheseagreementsalsorequireustomaintainspecifiedratingsandfinancial ratios, includingaminimumnetworthcovenant. If wefail tocomplywiththesecovenantsormeetrequiredfinancial ratios, thelendersorcounterpartiesundertheseagreementscoulddeclareadefaultanddemandimmediaterepaymentofallamountsowedtothem.Asaresult,ourbusiness,financialconditionandoperatingresultscouldbeadverselyaffected.

Ifweareindefaultunderthetermsoftheseagreements,wemayalsoberestrictedinourabilitytodeclareorpayanydividends,redeem,purchaseoracquireanysharesormakealiquidationpaymentandareatriskofcross-defaultonotherarrangements.Inaddition,thecostandavailabilityofthesearrangementsvaryandanyadversechangeinthecostoravailabilityofsucharrangementscouldadverselyimpactourbusiness,financialconditionandoperatingresults.

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Regulatory Risks

Political, regulatory, governmental and industry initiatives may have a material adverse effect on our business, financial condition, results ofoperations, liquidity, cash flows and prospects.

Certain of the laws and regulations to which our Operating Subsidiaries are subject are summarized in Item 4, “Business Overview - Regulatory Matters.”Changesinthelawsandregulationsrelevanttoourbusinessmayhaveamaterialadverseeffectonourbusiness,financialcondition,resultsofoperations,liquidity,cashflowsandprospects. Thelawsandregulationsofthejurisdictionsinwhichourinsuranceandreinsurancesubsidiaries aredomiciledrequire, amongotherthings,maintenanceofminimumlevelsofstatutorycapital,surplus,andliquidity;varioussolvencystandards;andperiodicexaminationsofsubsidiaries’financialcondition.Insomejurisdictions,lawsandregulationsalsorestrictpaymentsofdividendsandreductionsofcapital.Applicablestatutes,regulations,andpoliciesmayalsorestricttheabilityofthesesubsidiariestowriteinsuranceandreinsurancepolicies,tomakecertaininvestments,andtodistributefunds.

Some of these authorities regularly consider enhanced or new regulatory requirements intended to prevent future crises or otherwise assure the stability ofinstitutionsundertheirsupervision.Theseauthoritiesmayalsoseektoexercisetheirsupervisoryauthorityinnewandmorerobustways,andnewregulatorscouldbecome authorized to oversee parts of our business. The purpose of insurance laws and regulations generally is to protect policyholders and ceding insurancecompanies, not our shareholders or noteholders. Failure to comply with or obtain appropriate authorizations and/or exemptions under any applicable laws andregulationscouldresultinrestrictionsonourabilitytodobusinessorundertakeactivitiesthatareregulatedinoneormoreofthejurisdictionsinwhichweconductbusinessandcouldsubjectustofines,othersanctionsandreputationalinjury.In2020,weidentifiedthatAPJAssetProtectionJerseyLimited(“APJJersey”),ourJersey registered insurance company subsidiary, in connection with an intra-group outsourcing arrangement with Aspen U.K. Syndicate Services Limited(“AUKSSL”)(previouslyAPJServicesLimited),hadpotentiallycarriedouttheregulatedactivitiesofeffectingandcarryingoutcontractsofinsuranceasprincipalincontraventionofU.K.lawasitdidnothavethenecessarylicensesand/orauthorizationstoundertaketheseactivitiesintheU.K.WehavesincestoppedwritingnewbusinessviaAPJJersey,andexistingcontractsthatareinrun-offarebeinghandledbyanoutsourcedproviderwhoisauthorizedtodoso.OurregulatorsandLloyd’shavebeennotifiedand,whilenoformalregulatoryactionhasbeentakentodate,wecouldnonethelessbesubjecttoregulatorypenaltiesorcensure.WecouldalsobecomeliabletorepaythepremiumsreceivedfrompolicieswrittenbyAPJJerseyincontraventionofU.K.lawandcouldalsobeexposedtoclaimsforcompensationforconsequentiallosssufferedbypolicyholdersasaresultofhavingpaidpremiumsinrespectofsuchpolicies.

Itisnotpossibletopredictallfutureimpactsofpolitical,regulatory,governmentalorindustrychangesbuttheycouldaffectthewayweconductourbusinessandmanageourcapital,andmayrequireustosatisfyincreasedcapitalrequirementsortoincuradditionalexpenses,anyofwhich,inturn,couldaffectourresultsofoperations,financialconditionandliquidity.

The foreign and U.S. federal and state laws and regulations that are applicable to our operations are complex and may increase the costs of regulatorycomplianceorsubjectourbusinesstothepossibilityofregulatoryactionsorproceedings.Inadditiontoinsuranceandfinancialindustryregulations,ouractivitiesarealsosubjecttorelevanteconomicandtradesanctions,moneylaunderingregulations,andanti-corruptionlawsincludingtheU.S.ForeignCorruptPracticesActandtheU.K.BriberyAct2010,whichmayincreasethecostsofregulatorycompliance,limitorrestrictourabilitytodobusinessorengageincertainregulatedactivities,orsubjectustothepossibilityofregulatoryactions,proceedingsandfines.Wemaintainpoliciesandproceduresdesignedtocomplywiththeselawsandregulations.Aspartofourbusiness,wemay,fromtimetotime,engageinlimitedsalesandtransactionsinvolvingcertaincountriesthataretargetsofeconomicsanctions,providedthatsuchsalesandtransactionsareauthorizedpursuanttoapplicableeconomicsanctionslawsandregulations.However,wecannotpredictthenature,scopeoreffectoffutureregulatoryrequirements,includingchangesthatmayaffectexistingregulatoryauthorizations,andwecannotpredictthemannerinwhichexistinglawsandregulationsmightbeadministeredorinterpreted.Further,therecanbenoguaranteethatourpoliciesandprocedureswillbeeffectiveinpreventing violations, which could adversely affect our reputation, business, financial condition or results of operations. If in the future we are found to be inviolation of U.S. sanctions or export control laws, it could result in substantial fines and penalties for us. The insurance industry is also affected by political,judicial, and legal developments that may create new and expanded regulations and theories of liability. The current economic and financial climates presentadditionaluncertaintiesandrisksrelatingtoincreasedregulationandthepotentialforincreasedinvolvementoftheU.S.andothergovernmentsinthefinancialservicesindustry.

In the event or absence of changes in applicable laws and regulations in particular jurisdictions, we may from time to time face challenges, or changes inapproach to oversight of our business from insurance or other regulators, including challenges resulting from implementing new or additional processes orproceduresthatcannotbequicklyadaptedtoaddressnewregulatoryrequirements.Moreover,wecouldbe,orouremployeesactingonourbehalf,couldbefoundtohaveviolatedexistinglaws,rulesorregulations.Ourregulatorshavetheabilitytomakeregulatoryinterventionsusingtheir

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powers, including through investigations, requests for data and analysis, interviews or reviews (including skilled persons reports under section 166 of FSMA),whichregulatoryinterventionmayrequirespecificremediation, includingviaguidanceonaconfidential basis, inrespectofhistorical practices, changestoourexisting practices, public censure, the loss or restriction of regulatory permissions necessary to carry out our business in the same manner as before, and/oradditionalregulatorycapitaltobeheld.

Weareinvolvedinperiodicmeetingswith,andreviewsby,regulators,pursuanttowhichtheyreviewourbusinessandprovidechallengesinordertotestandvalidatethesupervisoryandworkplanadoptedbytheirsupervisoryteams.Throughsuchprocesses, ourregulatorsmayvalidateand/orchallenge,amongotherthings,ourstrategy,businessplans,internalgovernance,riskandcapitalmanagementandcomplianceframeworks.Ourregulatorshaverequiredus,andweareunder continuing obligations, to remediate failures, weaknesses and other issues that they have identified, including, but not limited to, with respect to ourunderwritingperformance,reservingriskandcapitalmanagement,andgovernance,which,ifweareunsuccessfulinremediatingcouldresultingreaterregulatoryintrusion, enforcement action and/or the exercise of our regulators’ own initiative powers (including imposing restrictions on our underwriting and/or arequirementtomaintainadditionalcapital,whichwouldreduceourunderwritingcapacity).Wearecurrentlyintheprocessofimplementinginitiativestoimproveour business, including our underwriting performance, risk and capital management and governance, which, if we are unable to successfully implement couldresultingreaterregulatoryintrusionand/orenforcementactionortheexerciseofourregulators’owninitiativepowers,whichcouldhaveamaterialadverseeffectonourbusiness,resultsofoperationsandfinancialcondition.

Webelieveitislikelytherewillcontinuetobeincreasedregulationof,andotherformsofgovernmentparticipationin,ourindustryinthefuture,whichcouldmaterially adverselyaffect our business by, amongother things: providingreinsurance capacity inmarkets andto policyholders that wetarget or requiringourparticipationinindustrypoolsandguarantyassociations;furtherrestrictingouroperationalorcapitalflexibility;expandingthescopeofcoverageunderexistingpolicies;regulatingthetermsofour(re)insurancepolicies;adoptingfurtherorchangingcompliancerequirementswhichmayresultinadditionalcostswhichmayadverselyimpactourresultsofoperation;ordisproportionatelybenefitingthecompaniesdomiciledinonecountryoverthosedomiciledinanother.

Changes in regulations that adversely affect the U.S. mortgage insurance and reinsurance market could affect our operations significantly and couldreduce the demand for mortgage insurance.

Inadditiontothegeneralregulatoryriskstowhichwearesubject,thereinsurancewewritecouldalsobeindirectlyaffectedbyvariousadditionalregulationsrelatingparticularlytoourU.S.mortgagereinsuranceoperations.U.S.federalandstateregulationsaffectthescopeofoperationsofmortgageguarantyinsurersandcommercialcreditinsurers,towhomweprovidecreditreinsurance.Legislativeandregulatorychangescouldcausedemandforprivatemortgageinsurancetodecrease,whichcouldhaveanadverseimpactonourU.S.mortgagereinsuranceoperations.IncreasesinthemaximumloanamountthattheU.S.FederalHousingAdministrationcaninsure,andreductionsinthemortgageinsurancepremiumsitcharges,canreducethedemandforprivatemortgageinsurance.Decreasesinthemaximum loan amounts government-sponsored enterprises, such as the Federal National Mortgage Association (Fannie Mae) and the Federal Home LoanMortgageCorporation(FreddieMac)(the“GSEs”),willpurchaseorguarantee,increasesinGSEfees,ordecreasesinthemaximumloan-to-valueratioforloanstheGSEswillpurchase,canalsoreducedemandforprivatemortgageinsurance.ChangesintheselawsorregulationscouldhaveanindirectadverseimpactontheprofitabilityofourU.S.mortgagereinsurancebusiness.

The United Kingdom’s withdrawal from the E.U. could adversely impact our business, results of operations and financial condition.TheCompanyfacesnewregulatorycostsandchallengesasaresultofBrexit.TheU.K.lefttheE.U.asofJanuary31,2020andeconomicrelationsbetweenthe

U.K.andtheE,U.arenowgovernedbyaTradeandCooperationAgreementwhichislimitedinscopeandcontainsveryfewspecificprovisionsrelatingtoinsuranceandfinancialservices.Asaresult,AspenU.K.haslostitsfinancialservicespassportswhichprovideditthelicensetooperateacrossborderswithintheEuropeanEconomicArea(“EEA”)withoutobtaininglocalregulatoryapprovalwhereinsurersandcedantsarelocated.TheCompany’sEEALloyd’soperationsareabletocontinuethroughLloyd’sBrussels,however,operationalandcapitalrequirementsrelatingtheretomightresultinincreasedcostsorFundsatLloyd’s(asdefinedbelowinLloyd’s Regulation)andmightnotprovidethesameaccesstomarketsthattheCompanycurrentlyrequirestoconductbusinessintheEEA.Inaddition,theabilitytoaccesstheE.U.marketthroughourLloyd'sSyndicatedependsonLloyd'sbeingabletocomplywithE.U.regulationsthroughitsBelgiumsubsidiary.Specifically,Lloyd’sisstillindiscussionwiththeBelgiumFinancialServicesMarketsAuthorityandtheNationalBankofBelgiumregardingtheLloyd’sEuropeoperatingmodelandtheactivitiesperformedforitbymanagingagents(throughtheOutsourcingAgreement)andthequestionofwhetheritwaspossiblethattheycouldbeconstruedasconstitutinginsurancedistributionundertheInsuranceDistributionDirective,which

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wouldthereforerequirethemtobeauthorizedwithintheEEA.Lloyd’sareproposingtomakechangestotheoperatingmodelbythesecondhalfof2021withtheengagementofthemarket.

WhilewehaveimplementedchangesinouroperationstoaccommodateBrexit,thefullextenttowhichourbusiness,operationsandfinancialconditioncouldbeadverselyaffectedbyBrexitisuncertain.TheimpactoftheU.K.’swithdrawalontheU.K.andEuropeaneconomiesandthebroaderglobaleconomycouldbesignificant,resultinginincreasedvolatilityandpotentiallylowereconomicgrowthandinstabilityinthefinancialandforeignexchangemarkets.Wemayhavetoreviewourunderwritingplatformsandincuradditionalregulatorycostsasaresult.

Changes in current accounting practices and future pronouncements may materially impact our reported financial results.

Unanticipateddevelopmentsinaccountingpracticesmayrequireustoincurconsiderableadditionalexpensestocomplywithsuchdevelopments,particularlyifwearerequiredtoprepareinformationrelatingtopriorperiodsforcomparativepurposesortoapplythenewrequirementsretroactively.Suchdevelopmentsmayalsosignificantlyimpactthepresentationofsuchfinancial statementsandmayrequirerestatements. Theimpactofchangesincurrent accountingpracticesandfuturepronouncementscannotbepredictedbuttheymayaffectthecalculationofnetincome,netequityandotherrelevantfinancialstatementlineitems.

Other Operational Risks

We could be adversely affected by the loss of one or more of our senior underwriters or other key employees or by an inability to attract and retain seniorstaff.

Oursuccesshasdependedandwillcontinuetodepend,insubstantialpart,onourabilitytoattractandretainourteamsofunderwritersinvariousbusinesslinesandother keyemployees. Thelossof oneormoreofour senior underwriters couldadverselyimpact ourbusinessby, for example, makingit moredifficult toretainclientsorotherbusinesscontactswhoserelationshipdependsinpartontheserviceofthedepartingpersonnel.Ingeneral, thelossofkeyservicesofanymembersofourcurrentunderwritingteamsmayadverselyaffectourbusinessandoperatingresults.

We also rely substantially upon the services of our senior management team. Although we have employment agreements with all members of our seniormanagementteam,if weweretounexpectedlylosetheservicesofoneormoreofourseniormanagementteamorotherkeypersonnel, ourbusinessorratingscouldbeadverselyaffected.Forexample,anunplannedchangeinourseniormanagementteamcouldcauseariskofdisruptiontoourbusinessincluding,butnotlimited to, our underwriting, claims handling, reserving and financial reporting functions. We do not currently maintain key-man life insurance policies withrespecttoanyofouremployees.

We rely on the execution of internal processes to maintain our operations and the operational risks that are inherent to our business, including thoseresulting from fraud or employee errors or omissions, may result in financial losses.

Werelyontheaccurateexecutionofinternalprocessestomaintainouroperations.Weseektomonitorandcontrolourexposuretorisksarisingfromtheseprocessesthroughariskcontrolframeworkencompassingavarietyofreportingsystems,internalcontrols,managementreviewprocessesandothermechanisms.Wecannotprovideabsoluteassurancethattheseprocessesandprocedureswilleffectivelycontrolallknownrisksoreffectivelyidentifyunforeseenrisks,orthatouremployeesandthird-partyagentswilleffectivelyimplementthem.Lossmayresultfrom,amongotherthings,fraud,errors,failuretodocumenttransactionsproperly, failure to obtain proper internal authorization, failure to comply with underwriting or other internal guidelines or failure to comply with regulatoryrequirements.Lossfromtheseriskscouldadverselyaffectourbusiness,resultsofoperationsandfinancialcondition.Inaddition,insurancepoliciesthatwehaveinplacewiththirdpartiesmaynotprotectusintheeventthatweexperienceasignificantlossfromtheserisks.

A failure in our operational systems or infrastructure or those of third parties, including those caused by security breaches or cyber-attacks could disruptour business, damage our reputation and cause losses.

Ouroperationsrelyonthesecureprocessing,storage,andtransmissionofconfidentialandotherinformationandassets,includinginourcomputersystemsandnetworks.Ourbusiness,includingourabilitytoadequatelypriceproductsandservices,establishreserves,provideaneffectiveandsecureservicetoourcustomers,valueourinvestmentsandreportourfinancialresultsinatimelyandaccuratemanner,dependssignificantlyontheintegrity,availabilityandtimelinessofthedatawemaintain,aswellasthedataandassetsheldthroughthird-partyoutsourcers,serviceprovidersandsystems.Cybersecurityandtechnologythreatscanincludephishingscams,accounttakeovers,introductionsofmalware,attemptsatelectronicbreak-ins,andthecomputerizedsubmissionoffraudulentand/orduplicativepaymentrequests.Anysuchbreaches

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orinterference(includingattemptedbreachesorinterference)bythirdpartiesorbyinsidersthatmayoccurinthefuturecouldhaveamaterialadverseimpactonourbusiness,reputation,financialconditionorresultsofoperations.

Inanefforttoensuretheintegrityofsuchdata,weimplementnewsecuritymeasuresandsystemsandimproveorupgradeourexistingsecuritymeasuresandsystems on a continuing basis. Although we have implemented administrative and technical controls and take protective actions to reduce the risk of cyberincidentsandtoprotectourinformationtechnologyandassets, andweendeavortomodifysuchproceduresascircumstanceswarrantandnegotiateagreementswiththird-partyproviderstoprotectourassets,suchmeasuresmaybeinsufficienttoprevent,amongotherthings,unauthorizedaccess,computerviruses,malwareor other malicious code or cyber-attack, catastrophic events, system failures and disruptions (including in relation to new security measures and systems),employee errors or malfeasance, third-party (including outsourced service providers) errors or malfeasance, loss of assets and other security events (each, a“SecurityEvent”).Likeotherglobalcompanies,wehavefromtimetotimeexperienced,andarelikelytocontinuetobesubjectto,SecurityEvents,noneofwhichtodatehavehadamaterialadverseimpactonourbusiness,resultsofoperationsorfinancialcondition.Asthebreadthandcomplexityofoursecurityinfrastructurecontinuestogrow,thepotentialriskofaSecurityEventincreases.IfadditionalSecurityEventsoccur,theseeventsmayjeopardizeourorourpolicyholders’orcounterparties’confidentialandotherinformationprocessedandstoredwithus,andtransmittedthroughourcomputersystemsandnetworkspotentiallyresultingin a violation of applicable privacy, data protection or other laws, or otherwise cause interruptions, delays, or malfunctions in our, our policyholders’,counterparties’ or thirdparties’ operations, orresult indatalossorlossofassets whichcouldresult insignificant lossesand/orfines, reputational damageoramaterial adverse effect on our business, financial condition or operating results. We may be required to expend significant additional resources to modify ourprotective measures or to investigate and remediate vulnerabilities or other exposures and to pursue recovery of lost data or assets and we may be subject tolitigationandfinancial losses. Wecurrentlymaintaincyberliabilityinsurancethat providesthird-partyorfirst partyliability coveragestoprotect us, subject topolicylimitsandcoverages,againstcertaineventsthatcouldbeaSecurityEvent.However,aSecurityEventcouldnonethelesshaveamaterialadverseeffectonouroperatingresultsorfinancialcondition.

Despite the contingency plans and facilities we have in place and our efforts to observe the regulatory requirements surrounding information security, ourabilitytoconductbusinessmaybeadverselyaffectedbyadisruptionoftheinfrastructurethatsupportsourbusinessinthecommunitiesinwhichwearelocated,orofoutsourcedservicesorfunctions,includingadisruptioninvolvingelectrical,communications,transportation,orotherservicesweuse.Ifadisruptionoccursinonelocationandouremployeesinthatlocationareunabletooccupyourofficesandconductbusinessorcommunicatewithortraveltootherlocations,ourabilitytoserviceandinteractwithpolicyholdersmaysufferandwemaynotbeabletosuccessfullyimplementcontingencyplansthatdependoncommunicationortravel.Ifsustainedorrepeated,suchbusinessinterruption,systemfailure,servicedenialordatalossand/ordamagecouldresultinadeteriorationofourabilitytowriteandprocessbusiness,providecustomerservice,payclaimsinatimelyfashionorperformothernecessarybusinessfunctions.

Evolving privacy and data security regulations could damage our reputation and cause losses.

Regulatoryauthorities aroundtheworldhaveimplementedorareconsideringanumberoflegislativechangesorregulationsconcerningdataprotectionandcybersecuritywhichhaverequiredormayrequireustoincuradditionalexpenses.WearesubjecttonumerousU.S.federalandstatelawsandnon-U.S.regulationsgoverningtheprotectionofpersonalandconfidentialinformationofourclientsoremployees,includinginrelationtomedicalrecordsandfinancialinformation.Existingcybersecurityregulationsvarybyregionorcountryinwhichweoperateandcoverdifferentaspectsofbusinessoperations.

Our business is subject to the E.U. General Data Protection Regulation (“E.U. GDPR”) which regulates data protection for all individuals within the E.U.,includingforeigncompaniesprocessingdataofindividualsintheE.U.;itenhancesindividuals’rights,introducescomplexandfar-reachingcompanyobligationsandincreasespenaltiessignificantlyincaseofviolation.TheE.U.GDPRsetsoutanumberofrequirementsthatmustbecompliedwithwhenhandlingpersonaldataincluding:theobligationtoappointdataprotectionofficersincertaincircumstancesandtheprincipalofaccountabilityandtheobligationtonotifysupervisoryauthoritiesandindividualsofpersonaldatabreachesincertaininstances.TheinterpretationandapplicationofdataprotectionlawsintheU.S.,Europe,Bermudaandelsewherearedevelopingandareoftenuncertainandinflux.It ispossiblethattheselawsorcybersecurityregulationsmaybeinterpretedandappliedinamannerthat is inconsistent withourdataprotectionorsecuritypractices. If so, inadditiontothepossibilityoffines, adatasupervisoryauthoritymayissueanorderrequiringthatwechangeourdatapractices,whichcouldhaveanadverseeffectonourbusinessandresultsofoperations.Complyingwiththesevariouslawswillcauseustoincuradditionalcostsandcouldrequireustochangeourbusinesspractices.

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TheE.U.GDPRalsoprohibitstheinternationaltransferofpersonaldatafromtheEEA/U.K.tocountriesoutsideoftheEEA/U.K.unlessmadetoacountrydeemedtohaveadequatedataprivacylawsbytheEuropeanCommissionorU.K.Governmentoradatatransfermechanismhasbeenputinplace.InJuly2020,theCourtofJusticeoftheEuropeanUnion(“CJEU”)initsSchremsIIrulinginvalidatedtheE.U.-U.S.PrivacyShieldframework,aself-certificationmechanismthat facilitated the lawful transfer of personal data fromthe EEA/U.K. to the United States, with immediate effect. The CJEUupheld the validity of standardcontractual clauses (“SCCs”) as a legal mechanism to transfer personal data but companies relying on SCCs will need to carry out a transfer privacy impactassessment,whichamongotherthings,assesseslawsgoverningaccesstopersonaldataintherecipientcountryandconsiderswhethersupplementarymeasuresthatprovideprivacyprotectionsadditionaltothoseprovidedunderSCCswillneedtobeimplementedtoensureanessentiallyequivalentlevelofdataprotectiontothataffordedintheEEA.Thismayhaveimplicationsforourcross-borderdataflowsandmayresultincompliancecosts.

Althoughwestrivetocomplywithallapplicabledataprotectionlawsandregulations,itispossiblethatwemayfailtocomplywithallapplicablelawsandregulations. The failure or perceived failure to comply may result in inquiries and other proceedings or actions against us by government entities or otherregulators,includingmonetaryfees,orcouldcauseustoloseclientswhichcouldpotentiallyhaveanadverseeffectonourbusinessandresultsofoperations.

Our internal controls over financial reporting may have gaps or other deficiencies.

Operational risk and losses can result from, among other things, fraud, errors, failure to document transactions properly or to obtain proper internalauthorization,failuretocomplywithregulatoryrequirements,informationtechnologyfailuresandfailuretoappropriatelytransitionnewhiresorexternalevents.We continue to enhance our operating procedures and internal controls (including information technology initiatives and controls over financial reporting) toeffectively support our businessandourregulatoryandreportingrequirements. Refer toItem15“ChangesinInternal Controls over Financial Reporting.” Ourmanagement does not expect that our disclosure controls or our internal controls will prevent all errors and all fraud. A control system, no matter how wellconceivedandoperated, canprovideonlyreasonable, not absolute, assurancethat theobjectives of thecontrol systemaremet. Further, thedesignof a controlsystemmustreflectthefactthatthereareresourceconstraints,andthebenefitsofcontrolsmustbeconsideredrelativetotheircosts.Asaresultoftheinherentlimitationsinallcontrolsystems,noevaluationofcontrolscanprovideabsoluteassurancethatallcontrolissuesandinstancesoffraud,ifany,withinthecompanyhavebeendetected. Theseinherent limitationsincludetherealities that judgmentsindecisionmakingcanbefaulty, andthat breakdownscanoccurbecauseofsimpleerrorormistake.Additionally,controlscanbecircumventedbytheindividualactsofsomepersonsorbycollusionoftwoormorepeople.Thedesignofanysystemof controls alsois basedinpart uponcertain assumptions about thelikelihoodof future events, andthere canbenoassurancethat anydesignwillsucceedin achievingits stated goals under all potential future conditions; over time, controls maybecomeinadequate becauseof changes in conditions, or thedegreeofcompliancewiththepoliciesorproceduresmaydeteriorate.Asaresultoftheinherentlimitationsinacost-effectivecontrolsystem,misstatementduetoerrororfraudmayoccurandnotbedetected.

Our internal control system is designed to provide reasonable assurance regarding the reliability of financial reporting and the preparation of financialstatementsforexternal purposesinaccordancewithgenerallyacceptedaccountingprinciples. However, ourinternal controlsoverfinancial reportingmayhavegapsor other deficiencies. Weidentified a material weakness in internal control over financial reportingduringthe fourth quarter of 2019, as describedin ourannualreportfortheyearendedDecember31,2019.Remedialcontrolswereimplementedduringthefirstquarterof2020andduringthefourthquarterof2020,the remedial controls were tested and the Company’s management concluded that such material weakness had been fully remediated, however there is noguarantee that future significant deficiencies or material weaknesses in internal controls may not occur. Any such gaps or deficiencies may require significantresources to remediate and may also expose us to litigation, regulatory fines or penalties, or other losses. Inadequate process design or a failure in operatingeffectivenesscouldresultinamaterialmisstatementofourfinancialstatementsdueto,butnotlimitedto,poorlydesignedsystems,changesinend-usercomputing,poorly designed IT reports, ineffective oversight of outsourced processes, failure to perform relevant management reviews, accounting errors or duplicatepayments,anyofwhichcouldresultinarestatementoffinancialaccounts.

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We use analytical models to assist our decision making in key areas such as underwriting, claims, reserving, and catastropherisks but actual resultscould differ materially from the model outputs and related analyses.

We have made substantial investments to develop proprietary analytic and modeling capabilities to facilitate our underwriting, risk management, capitalmodelingandallocation, andriskassessments relatingtotherisksweassume. Wealsousevendormodelswhereavailable and, whereappropriate, weuseourproprietary model in combination with vendor models. These models and other tools help us to manage our risks, understand our capital utilization and riskaggregation,informmanagementandotherstakeholdersofcapitalrequirementsandseektoimprovetherisk/returnprofileoroptimizetheefficiencyoftheamountof capital weapply to cover the risks in the individual contracts wesell andin our portfolio as a whole. However, giventhe inherent uncertainty of modelingtechniques and the application of such techniques, the possibility of human or systems error, the challenges inherent in consistent application of complexmethodologiesinafluidbusinessenvironmentandotherfactors,ourmodels,toolsanddatabasesmaynotaccuratelyaddresstheriskswecurrentlycoverortheemergenceofnewmatterswhichmightbedeemedtoimpactcertainofourcoverages.

Furthermore, there are risks associated with catastrophic events, which are either poorly represented or not represented at all by analytical models. Eachmodelingassumptionorun-modeledriskintroducesuncertaintyintotheestimates that management must consider. Theseuncertainties caninclude, but arenotlimitedto,thefollowing:

– Themodelsdonotaddressallthepossiblehazardcharacteristicsofacatastropheperil(e.g.,theprecisepathandwindspeedofahurricane);– Themodelsmaynotaccuratelyreflectthetruefrequencyofevents;– Themodelsmaynotaccuratelyreflectarisk’svulnerabilityorsusceptibilitytodamageforagiveneventcharacteristic;– Themodelsmaynotaccuratelyrepresentlosspotentialtoreinsurancecontractcoveragelimits,termsandconditions;and– Themodelsmaynotaccuratelyreflecttheimpactontheeconomyoftheareaaffectedorthefinancial,judicial,political,orregulatoryimpactoninsurance

claimpaymentsduringorfollowingacatastropheevent.

Accordingly,ourmodelsmayunderstatetheexposuresweareassuming.Conversely,ourmodelsmayprovetooconservativeandcontributetofactorswhichmayimpedeourabilitytogrowinrespectofnewmarketsorperilsorinconnectionwithourcurrentportfolioofcoveragesorthelossenvironmentotherwisemayprovemorebenignthanourcapitalloadingforcatastrophesorothermodeledlosses.Insuchcaseofexcesscapital,wewouldmakeajudgmentaboutredeployingthe capital in lines of businesses or pursuingother capital management activities, suchas dividends or share repurchases, whichjudgment will also dependonmodelingtechniquesandresults.Ifcapitalmodelsproveinadequate,ourresultofoperationsandfinancialconditionmaybemateriallyadverselyimpacted.

Risks Related to Our Preference Shares

Our controlling shareholder owns all of our ordinary shares and has the power to determine the affairs of the Company, including in ways not favorableto the interests of holders of the preference shares.

Parent owns 100%of the ordinary shares of the Company. As a result, Parent has power to elect our directors and to determine the outcomeof any actionrequiringshareholderapproval.Parent’sinterestsmaydifferfromtheinterestsoftheholdersofthepreferencesharesand,givenParent’scontrollinginterestintheCompany,circumstancesmayariseunderwhichitmayexerciseitscontrolinamannerthatisnotfavorabletotheinterestsoftheholdersofthepreferenceshares.

Our ability to pay dividends or to meet ongoing cash requirements may be constrained by our holding company structure.

AspenHoldingsisaholdingcompanyand,assuch,wedonotexpectittohaveanysignificantoperations.Itsassetsprimarilyconsistofownershipofthesharesof our subsidiaries, including our Operating Subsidiaries, a portfolio of fixed incomesecurities, and cash and cash equivalents. Dividends and other permitteddistributionsandloansfromourOperatingSubsidiariesareexpectedtobeoursolesourceoffundstomeetongoingcashrequirements,includingourdebtservicepayments andother expenses, anddividendpayments, to our preference shareholders andour Parent, as appropriate. OurOperating Subsidiaries are subject tocapital,regulatoryandotherrequirementsthatinformtheirabilitytodeclareandpaydividendsandmakeloanstootherAspenGroupcompanies.RefertoItem4,“BusinessOverview—RegulatoryMatters—BermudaRegulation—RestrictionsonDividends,DistributionsandReductionofCapital,”“BusinessOverview—RegulatoryMatters—U.K.andE.U.Regulation—RestrictionsonDividendPayments,”and“BusinessOverview—RegulatoryMatters—U.S.Regulation—StateDividendLimitations”belowand“OperatingandFinancialReviewandProspects—LiquidityandCapitalResources”inItem5belowformoreinformationonourabilitytopaydividends.These

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andotherrequirementsmaymeanthatourOperatingSubsidiariesareunabletopaysufficientdividendstoenableustomeetourongoingcashrequirements,whichcouldmateriallyadverselyaffectourliquidityorfinancialcondition.

Certain regulatory and other constraints may limit our ability to pay dividends on our securities.

We are subject to Bermuda regulatory constraints that affect our ability to pay dividends and make other distributions on our preference shares or othersecurities. Under the Bermuda Companies Act 1981, as amended (the “Companies Act”), we may declare or pay a dividend or distribution out of contributedsurplus only if we have reasonable grounds to believe that we are, and would after the payment be, able to meet our liabilities as they become due or if therealizablevalueofourassetswouldtherebynotbelessthanourliabilities.RefertoItem4,“BusinessOverview—RegulatoryMatters”,Item5,“OperatingandFinancialReviewandProspects—LiquidityandCapitalResources”andItem18,Note13ofourconsolidatedfinancialstatements,“StatutoryRequirementsandDividendsRestrictions”formoreinformationonourabilitytopaydividends.

U.S. persons who own our securities may have more difficulty in protecting their interests than U.S. persons who are shareholders of a U.S. corporation.

TheCompaniesAct,whichappliestous,differsinsomematerialrespectsfromlawsgenerallyapplicabletoU.S.corporationsandtheirshareholders.Thesedifferencesinclude,butarenotlimitedto,themannerinwhichdirectorsmustdisclosetransactionsinwhichtheyhaveaninterest, therightsofshareholderstobringclassactionandderivativelawsuits,thescopeofindemnificationavailabletodirectorsandofficersandprovisionsrelatingtotheamalgamations,mergersand acquisitions and takeovers. Holders of our preference shares may therefore have more difficulty protecting their interests than would shareholders of acorporationincorporatedinajurisdictionwithintheU.S.

Generally,thedutiesofdirectorsandofficersofaBermudacompanyareowedtothecompanyonly.ShareholdersofBermudacompaniestypicallydonothaverightstotakeactionagainstdirectorsorofficersofthecompanyandmayonlydosoinlimitedcircumstances.ClassactionsandderivativeactionsaretypicallynotavailabletoshareholdersunderBermudalaw.TheBermudacourts,however,wouldordinarilybeexpectedtopermitashareholdertocommenceanactioninthenameofacompanytoremedyawrongtothecompanywheretheact complainedofisallegedtobebeyondthecorporatepowerofthecompanyorillegal, orwouldresultintheviolationofthecompany’smemorandumofassociationorbye-laws.Furthermore,considerationwouldbegivenbyaBermudacourttoactsthatareallegedtoconstitute afraudagainst theminorityshareholders or, for instance, whereanact requires theapproval ofagreater percentageofthecompany’sshareholdersthanthatwhichactuallyapprovedit.Whentheaffairsofacompanyarebeingconductedinamannerthatisoppressiveorprejudicialtotheinterestsof some shareholders, one or more shareholders may apply to the Supreme Court of Bermuda, which may make such order as it sees fit, including an orderregulatingtheconductofthecompany’saffairsinthefutureororderingthepurchaseofthesharesofanyshareholdersbyothershareholdersorbythecompany.Additionally,underourbye-lawsandaspermittedbyBermudalaw,eachshareholderhaswaivedanyclaimorrightofactionagainstourdirectorsorofficersforanyactiontakenbydirectorsorofficersintheperformanceoftheirduties,exceptforactionsinvolvingfraudordishonesty.Inaddition,therightsofholdersofoursecurities and the fiduciary responsibilities of our directors under Bermuda law are not as clearly established as under statutes or judicial precedent in U.S.jurisdictions,particularlytheStateofDelaware.

We are a Bermuda company and it may be difficult to effect service of process on us or enforce judgments against us or our directors and executiveofficers in the United States.

WeareincorporatedunderthelawsofBermudaandourbusinessisbasedinBermuda.Inaddition,certainofourdirectorsandofficersresideoutsidetheUnitedStates,andasubstantialportionofourassetsandtheassetsofsuchpersonsarelocatedinjurisdictionsoutsidetheUnitedStates.Assuch,itmaybedifficultorimpossible to effect service of process upon us or those persons in the United States or to recover against us or themon judgments of U.S. courts, includingjudgmentspredicateduponcivilliabilityprovisionsoftheU.S.federalsecuritieslaws.

We have been advised by Bermuda counsel that there is no treaty in force between the U.S. and Bermuda providing for the reciprocal recognition andenforcementofjudgmentsincivilandcommercialmatters.Asaresult,whetheraU.S.judgmentwouldbeenforceableinBermudaagainstusorourdirectorsandofficers depends on whether the U.S. court that entered the judgment is recognized by the Bermuda court as having jurisdiction over us or our directors andofficers,asdeterminedbyreferencetoBermudaconflictoflawrules.AjudgmentdebtfromaU.S.courtthatisfinalandforasumcertainbasedonU.S.federalsecuritieslawswillnotbeenforceableinBermudaunlessthejudgmentdebtorhadsubmittedtothejurisdictionoftheU.S.court,andtheissueofsubmissionandjurisdictionisamatterofBermuda(notU.S.)law.

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Inadditiontoandirrespectiveofjurisdictionalissues,theBermudacourtswillnotenforceaU.S.federalsecuritieslawthatiseitherpenalorcontrarytopublicpolicyinBermuda.ItistheadviceofourBermudacounselthatanactionbroughtpursuanttoapublicorpenallaw,thepurposeofwhichistheenforcementofasanction,powerorrightattheinstanceofthestateinitssovereigncapacity,willnotbeentertainedbyaBermudacourt.CertainremediesavailableunderthelawsofU.S.jurisdictions,includingcertainremediesunderU.S.federalsecuritieslaws,wouldnotbeavailableunderBermudalaworenforceableinaBermudacourt,astheywouldbecontrarytoBermudapublicpolicy.Further,noclaimmaybebroughtinBermudaagainstusorourdirectorsandofficersinthefirstinstanceforviolationofU.S.federalsecuritieslawsbecausetheselawshavenoextraterritorialjurisdictionunderBermudalawanddonothaveforceoflawinBermuda.ABermudacourtmay,however,imposecivilliabilityonusorourdirectorsandofficersifthefactsallegedinacomplaintconstituteorgiverisetoacauseofactionunderBermudalaw.

Risks Related to Taxation

Our non-U.S. companies may be subject to U.S. federal income tax on their net income, which may have a material adverse effect on our operating resultsand your investment.

AspenHoldingsanditsnon-U.S.subsidiaries(otherthanAULandAspenU.K.)intendtomanagetheirbusinesssothattheyarenottreatedasengagedinatradeorbusinesswithintheUnitedStatesandthusnotsubjecttoU.S.federalincometaxontheirnetincome.However,becausethereisconsiderableuncertaintyastotheactivities whichconstitute beingengagedina tradeor business withintheUnitedStates, wecannot becertain that theU.S. Internal RevenueService(“IRS”) will not contendsuccessfully that oneor moreof these companies is engagedina tradeor business in theUnitedStates. If anyof thesecompanies isconsideredtobeengagedinatradeorbusinessintheUnitedStatesduringataxableyear, it generallywill besubject toU.S.federal incometax(includinganadditionalbranchprofitstax)onitsnetincomethatistreatedaseffectivelyconnectedwiththeconductofaU.S.tradeorbusinessforsuchyear(excepttotheextentanapplicableincometaxtreatyprovidesotherwise),inwhichcaseitsoperatingresultscouldbemateriallyadverselyaffected.

Our non-U.K. companies may be subject to U.K. tax that may have a material adverse effect on our operating results.

Noneofus,otherthanoursubsidiariesthatareincorporatedintheU.K.(the“U.K.Subsidiaries”),shouldbetreatedasbeingresidentintheU.K.forcorporationtaxpurposesexceptforAPJJerseywhich,althoughnotincorporatedintheU.K.,istreatedastaxresidentintheU.K.Eachofus,otherthantheU.K.SubsidiariesandAPJJersey,currentlyintendstomanageouraffairssothatnoneofus,otherthantheU.K.SubsidiariesandAPJJersey,isresidentintheU.K.fortaxpurposes.

AcompanythatisnotresidentintheU.K.forcorporationtaxpurposescanneverthelessbesubjecttoU.K.corporationtaxif it carriesonatradethroughapermanentestablishmentintheU.K.but,inthatcase,thechargetoU.K.corporationtaxislimitedtoprofits(bothrevenueprofitsandcapitalgains)attributabledirectlyorindirectlytosuchpermanentestablishment.

Eachofus,otherthantheU.K.SubsidiariesandAPJJersey,currentlyintendstooperateinsuchamannerthatnoneofus(otherthantheU.K.SubsidiariesandAPJ Jersey) carries on a trade through a permanent establishment in the U.K. Nevertheless, because neither case law nor U.K. statute completely defines theactivitiesthatconstitutetradingintheU.K.throughapermanentestablishment,HerMajesty’sRevenueandCustoms(“HMRC”)mightcontendsuccessfullythatanyofus(otherthantheU.K.SubsidiariesandAPJJersey)aretradingintheU.K.throughapermanentestablishment.

TheU.K.hasnoincometaxtreatywithBermuda.TherearecircumstancesinwhichcompaniesthatareneitherresidentintheU.K.norentitledtotheprotectionaffordedbyadoubletaxtreatybetweentheU.K.andthejurisdictioninwhichtheyareresidentmaybeexposedtoincometaxintheU.K.(otherthanbydeductionorwithholding)ontheprofitsofatradecarriedonthere,evenifthattradeisnotcarriedonthroughapermanentestablishment.However,eachofusintendstooperateinsuchamannerthatnoneofusfallswithinthechargetoincometaxintheU.K.(otherthanbydeductionorwithholding).

Ifanyofus,otherthantheU.K.SubsidiariesandAPJJersey,weretreatedasbeingresidentintheU.K.forU.K.corporationtaxpurposes,orascarryingonatradeintheU.K.,whetherornotthroughapermanentestablishment,ouroperatingresultscouldbemateriallyadverselyaffected.

Our U.K. operations may be affected by recent changes in U.K. and Australian tax law.

TheU.K.SubsidiariesandAPJJerseyshouldbetreatedasresidentintheU.K.andaccordinglybesubjecttoU.K.taxinrespectoftheirworldwideincomeandgains.AnychangeinthebasisorrateofU.K.corporationtaxcouldmateriallyadverselyaffecttheoperationsoftheU.K.residentcompanies.TheU.K.corporationtaxrateiscurrently19%.Achangeto

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themainU.K.corporationtaxratefrom19%to25%fromApril1,2023wasannouncedintheU.K.BudgetonMarch3,2021,howeverthishasnotyetbeenenactedintolaw.

TheOrganizationforEconomicCo-operationandDevelopment(“OECD”)publisheditsfinalreportsonBaseErosionandProfitShifting(“BEPSReports”)inOctober2015,containingrecommendationsonmeasurestocoordinatemultilateralactiononinternationaltaxrules.Recommendedactionsincludeensuringthattransferpricingoutcomesareinlinewithvaluecreation(notingthatthecurrentrulesmayfacilitatethetransferofrisksorcapitalawayfromcountrieswheretheeconomic activity takes place), neutralizing the effect of hybrid financial instruments and entities and limiting the deductibility of interest payments for taxpurposes.

InresponsetotheBEPSrecommendations,revisedtransferpricingguidelineshavebeenadoptedbytheU.K.andlegislationhasbeenintroducedbytheU.K.inrelationtohybridmismatches,thelatterofwhichcameintoeffectonJanuary1,2017.Legislationtorestricttaxdeductionsforinterestexpensesoflargegroups,inlinewiththeOECD’srecommendations,wasbroughtintoeffectfromApril1,2017.ThesechangestoU.K.taxlawinresponsetotheBEPSReportsmayhaveamaterialadverseeffectonourintra-groupfinancingarrangementsandourresults.

InMay2019,theOECDpublisheda“ProgrammeofWork”designedtoaddressthetaxchallengescreatedbyanincreasingdigitalizedeconomy.Thiswasdivided into two pillars. Pillar One addresses the broader challenge of a digitalized economy and focuses on the allocation of group profits among taxingjurisdictionsbasedonamarketbasedconceptratherthanthehistorical“permanentestablishment”concept.PillarTwoaddressestheremainingBEPSriskofprofitshiftingtoentities inlowtaxjurisdictionsbyintroducingaglobal minimumtaxandaproposedtaxonbaseerodingpayments, whichwouldoperate throughadenial of a deductionor impositionof source-basedtaxation(includingwithholdingtax) oncertain payments. In October 2020, the OECDreleaseda series ofdocuments regarding the ongoing work on Pillar One and Two, however significant elements remain unresolved and discussions are ongoing with a view toreachingpoliticalagreementbymid-2021,tothenbeincorporatedintolocaljurisdictiontaxlawsandtreatiessometimeshortlythereafter.Todate,notwithstandingtheexclusionfromPillar Oneoftheinsurancesector, theproposalhasbeenwrittenbroadlyenoughtopotentiallyapplytoouractivities, andtheimpacttotheCompanycannotbedeterminedatthistime.

LegislationrestrictingtheamountofU.K.profitinanyparticularaccountingperiodthatcanbeoffsetbyhistoricaltaxlosseswasbroughtintoeffectfromApril1,2017.Shouldutilizationofanytaxlossesbedelayedorrestrictedasaresultofthislegislation,thiscouldhaveamaterialadverseeffectonourresults.

TheU.K.divertedprofitstax(“DPT”)isseparatefromU.K.corporationtaxandischargedatahigherrateof25%.AchangetotherateofDPTfrom25%to31%fromApril1,2023wasannouncedintheU.K.BudgetonMarch3,2021,howeverthishasnotyetbeenenactedintolaw. Itisananti-avoidancemeasureaimedatprotectingtheU.K.taxbaseagainsttheartificialdiversionofprofitsthatarebeingearnedbyactivitiescarriedoutintheU.K.butwhicharenototherwisebeingtaxedintheU.K.,inparticularasaresultofarrangementsamongstcompaniesinthesamemultinationalgroup.TheU.K.’snetworkofdoubletaxtreatiesdoesnotofferprotectionfromaDPTcharge.Intheeventthattherulesapplytocertainarrangements,thenupfrontpaymentofHMRC’sestimateofthedeemedtaxliabilitymayberequired.IfanyofourU.K.ornon-U.K.companiesisliableforDPTasaresultofintra-grouparrangements,thiscouldhaveamaterialadverseeffectonourresults.

TheAustralianGovernmentannouncedanewdivertedprofitstaxwhichappliestotaxyearsbeginningonorafterJuly1,2017.Thedivertedprofitstaxissetat40%andismodeledontheU.K.’sDPT.IfAspenU.K.’sAustralianbranchisdeemedliableforAustralianDPTasaresultofintra-grouparrangements,thiscouldhaveamaterialadverseeffectonourresultsinfutureyears.

Our U.K. and U.S. operations may be adversely affected by a transfer pricing adjustment in computing U.K. or U.S. taxable profits.

AnyarrangementsbetweenU.K.-residententitiesoftheAspenGroupandothermembersoftheAspenGrouparesubjecttotheU.K.transferpricingregime.Consequently, if any agreement (including anyreinsurance agreements) betweena U.K.-resident entity of the AspenGroupandanyother AspenGroupentity(whetherthatentityisresidentinoroutsidetheU.K.)isfoundnottobeonarm’slengthtermsandasaresultaU.K.taxadvantageisbeingorhasbeenobtained,anadjustmentwillberequiredtocomputeU.K.taxableprofitsasifsuchanagreementwereorhadbeenonarm’slengthterms.SimilarrulesapplyintheU.S.andwouldhaveasimilarimpactonourU.S.residententitiesiftransferpricingadjustmentswererequired.AnytransferpricingadjustmentcouldadverselyimpactthetaxchargesufferedbytherelevantU.K.orU.S.residententitiesoftheAspenGroup.

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The BEPS Reports included a recommendation that groups should be required to report details of their operations and intra-group transactions in eachjurisdiction,knownascountrybycountryreporting(“CBCR”).TheU.K.hasimplementedtheserecommendationswitheffectfromJanuary1,2016.Itispossiblethatourapproachtotransferpricingmaybecomesubjecttogreaterscrutinyfromthetaxauthoritiesinthejurisdictionsinwhichweoperate,whichmayleadtotransferpricingauditsinthefuture.AnytransferpricingadjustmentcouldadverselyimpactthetaxchargesufferedbytherelevantentitiesoftheAspenGroup.

InApril2016,theE.U.issuedproposalstorequireallE.U.entities(includingbranches)topublishtheirCBCRreportsonwhichtheE.U.Parliamentvotedinfavorin2017andagainin2019,butwhichwereblockedbytheCompetitivenessCounciloftheE.U.laterin2019.Theproposals,ifeventuallyimplemented,arelikelytocauseincreasedauditactivityfromE.U.taxauthorities.LegislationhasbeenenactedgivingpowertointroduceregulationsrequiringpublicdisclosureofU.K.CBCRreports,althoughthispowerhasnotyetbeenexercised.

Recent and future changes in U.S. federal income tax law or the manner in which it is interpreted could materially adversely affect our results ofoperations.

TheTaxCutsandJobsActof2017(the“2017Act”)includescertainprovisionsintendedtoeliminatecertainperceivedtaxadvantagesofcompanies(includinginsurancecompanies)thathavelegaldomicilesoutsidetheUnitedStatesbuthavecertainU.S.connections,andU.S.personsinvestinginsuchcompanies.Forexample,the2017Actintroducedthebaseerosionandanti-abusetax(the“BEAT”),whichcouldmakeaffiliatereinsurancebetweenU.S.andnon-U.S.membersoftheAspenGroupeconomicallyunfeasible. Asdiscussedinmoredetailbelow,the2017Actalsorevisedcertainrulesapplicabletopassiveforeigninvestmentcompanies (“PFICs”) and controlled foreign corporations (“CFCs”). We are currently unable to predict the ultimate impact of the 2017 Act on our business,shareholdersandresultsofoperations,inpartbecausethe2017Actwillcontinuetoevolvethroughadditionalrulesandregulationswhichmayincreasethetaxliability of the U.S. members of the Aspen Group that reinsure with non-U.S. Aspen Group members and may impact the timing and amount of U.S. federalincometaxesimposedoncertainU.S.shareholders.Inaddition,itispossiblethatovertimetheBEAT,andthe2017Actgenerally,mayresultinincreasedpricesforcertainreinsuranceorinsuranceproductsandservices,whichcouldcauseadecreaseindemandforthem.Further,it ispossiblethat other legislation couldbeintroducedandenactedbythecurrentCongressorfutureCongresses,possiblywithretroactiveeffect,thatcouldhaveanadverseimpactonusorourshareholders.Theserecentandpotentialfuturechangesinlawcouldmateriallyadverselyaffectourbusiness,accesstocapital,financialconditionandresultsofoperations.

U.S. persons who hold 10% or more of the total voting power or value of our shares may be subject to U.S. federal income taxation on our undistributedearnings.

Ingeneral, a“10%U.S.Shareholder”(asdefinedbelow)ofanon-U.S.corporationthatisaCFCatanytimeduringataxableyearmustincludeinitsgrossincomeforU.S.federalincometaxpurposesitsproratashareoftheCFC’s“subpartFincome”and“testedincome”(withvariousadjustments)withrespecttoanyshares that such 10% U.S. Shareholder owns in such non-U.S. corporation (directly or indirectly through certain entities) on the last day in the non-U.S.corporation’staxableyearonwhichitisaCFC,evenifthesubpartFincomeortestedincomeisnotdistributed.A“10%U.S.Shareholder”generallyisaU.S.personthatowns(directly,indirectlythroughnon-U.S.entitiesorbyattributionbyapplicationoftheconstructiveownershiprulesofsection958(b)oftheU.S.InternalRevenueCodeof1986,asamended(the“Code”)(i.e.,“constructively”))atleast10%ofthetotalcombinedvotingpowerorvalueofallclassesofstockofanon-U.S.corporation.“SubpartFincome”ofaCFCgenerallyincludes“foreignpersonalholdingcompanyincome”(suchasinterest,dividendsandothertypesofpassiveincome),aswellasinsuranceandreinsuranceincome(includingunderwritingandinvestmentincome),andtestedincomeisgenerallyanyincomeoftheCFCotherthansubpartFincomeandcertainothercategoriesofincome.AnentitytreatedasaforeigncorporationforU.S.federalincometaxpurposesgenerallyisconsideredaCFCif“10%U.S.Shareholders”own(directly,indirectlythroughnon-U.S.entitiesorconstructively)morethan50%ofthetotalcombinedvotingpowerofallclassesofvotingstockofthatnon-U.S.corporationormorethan50%ofthetotalvalueofallstockofthatnon-U.S.corporation.However,forthepurposesoftakingintoaccountinsuranceincome,these50%thresholdsaregenerallyreducedto25%.

Wecurrently believe that AspenHoldings is not a CFC, due to the apparent dispersion of our share ownership. However, our shares maynot be as widelydispersedaswebelieve, andtheapplicationoftheindirect andconstructiveownershiprulesdependsuponfacts regardingourdirect andindirect shareholders,aboutwhichwehavelimitedinformation.Accordingly,noassurancecanbeprovidedthatAspenHoldingswillnotbeaCFC.Further,regardlessofwhetherAspenHoldingsisaCFC,mostorallofournon-U.S.subsidiariesaregenerallytreatedasCFCsbyreasonofcertainchangesintheconstructiveownershiprulesunderthe2017ActthatresultedinourU.S.subsidiariesgenerallybeingtreatedasconstructivelyowningthestockofournon-U.S.subsidiaries.Accordingly,any10%U.S.ShareholdersofAspenHoldingsmayberequiredto

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include in gross incomefor U.S. federal incometax purposes for eachtaxable year their pro rata shares of all or a portion of the subpart F incomeandtestedincomegeneratedbyournon-U.S.companies,regardlessofwhetheranydistributionsaremadetothem.Anysuch10%U.S.Shareholdersshouldconsulttheirowntaxadvisorsregardingtheapplicationoftheserulestothem.

U.S. persons who hold our shares may be subject to U.S. federal income taxation at ordinary income rates on their proportionate share of our relatedperson insurance income.

In general, if a non-U.S. corporation is a “RPII CFC”(as defined below) at any time during a taxable year, a U.S. person whoowns (directly or indirectlythroughcertainentities)anysharesofthenon-U.S.corporation(a“U.S.RPIIShareholder”)mustincludeinitsgrossincomeforU.S.federalincometaxpurposesitsproratashareofthenon-U.S.corporation’srelatedpersoninsuranceincome(“RPII”)withrespecttoanysharesthatsuchU.S.RPIIShareholderowns(directlyor indirectly through certain entities) on the last day in the non-U.S. corporation’s taxable year, even if the RPII is not distributed.Further, a U.S. RPIIShareholder’sproratashareofanyRPIIisdeterminedasifallRPIIforthetaxableyearweredistributedproportionatelyonlytoU.S.RPIIShareholdersonthatdate.Inaddition,aU.S.RPIIShareholderisrequiredtocomplywithcertainreportingrequirements,regardlessofthenumberofsharesownedbytheU.S.RPIIShareholder.

For these purposes, a “RPII CFC” generally is any non-U.S. corporation if U.S. RPII Shareholders collectively own (directly, indirectly through non-U.S.entitiesorconstructively)25%ormoreofthetotalcombinedvotingpowerofallclassesofstockofsuchcorporationentitledtovoteor25%ormoreofthetotalvalueofthestockofsuchcorporation.However,theRPIIrulesgenerallydonotapplywithrespecttoanon-U.S.corporationifeither(i)atalltimesduringitstaxableyearlessthan20%ofthetotalcombinedvotingpowerofallclassesofstockofthecorporationentitledtovoteandlessthan20%ofthetotalvalueofthecorporation is owned (directly or indirectly) by persons who are (directly or indirectly) insured under any policy of insurance or reinsurance issued by thecorporationorwhoarerelatedpersonstoanysuchperson(the“ownershipexception”), or(ii)theRPII(determinedonagrossbasis)ofthecorporationforthetaxableyearislessthan20%ofitsgrossinsuranceincomeforthetaxableyear(the“deminimisexception”).

Webelievethateachournon-U.S.OperatingSubsidiariesandeachofSilvertonReLtd.(“Silverton”),PeregrineandAPJJerseyisaRPIICFC.Nonetheless,weexpect that each such company will qualify for one or both of the ownership exception and the de minimis exception in the current taxable year and for theforeseeablefuture.However,theRPIIprovisionshaveneverbeeninterpretedbythecourts,andregulationsinterpretingtheRPIIprovisionsexistonlyinproposedform. It is not certain whether these regulations will be adopted in their proposed formor what changes or clarifications might ultimately be made thereto orwhetheranysuchchanges,aswellasanyinterpretationorapplicationoftheRPIIrulesbytheIRS,thecourts,orotherwise,mighthaveretroactiveeffect.TheU.S.TreasuryDepartmenthasauthoritytoimpose,amongotherthings,additionalreportingrequirementswithrespecttoRPII.Accordingly,themeaningoftheRPIIprovisionsandtheapplicationthereoftousisuncertain.Further,theapplicabilityoftheownershipanddeminimisexceptionsandtheRPIIrulesmoregenerallydepends upon facts regarding our direct and indirect shareholders and insureds, about which we have limited information. Accordingly, no assurances can beprovidedthatanyofourcompanieswillsatisfyeitherexception.Moreover,totheextenttheexceptionsdonotapply,wemaybeunabletocorrectlydeterminetheamountofRPIIthatanyU.S.RPIIShareholderisrequiredtotakeintoaccount.

U.S. persons who dispose of our shares may be subject to U.S. federal income taxation at the rates applicable to dividends on a portion of such disposition.

Section1248oftheCode,inconjunctionwiththeRPIIrules,generallyprovidesthatifaU.S.persondisposesofsharesinaRPIICFC(determinedwithoutregardtotheownershipordeminimisexceptions)thatwouldbetaxableasaninsurancecompanyundertheCodeifitwereaU.S.corporation,anygainfromthedispositionwillgenerallybetreatedasadividendtotheextentoftheholder’sshareofthecorporation’sundistributedearningsandprofitsthatwereaccumulatedduringtheperiodthattheholderownedtheshares(whetherornotsuchearningsandprofitsareattributabletoRPII).Inaddition,suchaholderwillberequiredtocomply with certain reporting requirements, regardless of the number of shares ownedby the holder. These RPII rules should not apply to dispositions of oursharesbecauseAspenHoldingswillnotitselfbedirectlyengagedintheinsurancebusiness.However,asdiscussedabove,thereisuncertaintyintheinterpretationoftheRPIIprovisionsandthusnoassurancescanbeprovided.

U.S. persons who hold our shares may be subject to adverse tax consequences if we are considered to be a PFIC.

IfAspenHoldingsischaracterizedasaPFIC,aU.S.personholdingsharesofAspenHoldingsgenerallywouldbesubjecttoanincreasedtaxliabilityatthetimeofthesaleatagainof,orreceiptofan“excessdistribution”withrespectto,theirshares.Inaddition,ifAspenHoldingsisconsideredaPFIC,uponthedeathofanyU.S.individualowningshares,such

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individual’sheirsorestatewouldnotbeentitledtoa“step-up”inthebasisofthesharesthatmightotherwisebeavailableunderU.S.federalincometaxlaws.Further,adistributionpaidbyAspenHoldingstoU.S.shareholdersthatischaracterizedasadividendandisnotcharacterizedasanexcessdistributionwillnotbeeligibleforreducedratesoftaxasqualifieddividendincomeifAspenHoldingsisconsideredaPFICinthetaxableyearinwhichsuchdividendispaidorwasaPFICintheprecedingtaxableyear.AU.S.shareholdermayalsobesubjecttoadditionalinformationreportingrequirements,includingthefilingofanIRSForm8621,ifAspenHoldingsisaPFIC.TheserulesgenerallywillapplytoaU.S.personifAspenHoldingswasaPFICatanytimeduringtheU.S.person’sholdingperiodwithrespecttoourshares.DifferentconsequencesmayapplyiftheU.S.personhaselectedtotreatAspenHoldingsasa“qualifiedelectingfund”oriftheU.S.personisa10%U.S.ShareholderofAspenHoldingsandAspenHoldingsisaCFC.

Ingeneral,anon-U.S.corporationwillbeaPFICduringagivenyearif(i)75%ormoreofitsgrossincomeconstitutes“passiveincome”(the“75%test”)or(ii)50%ormoreofitsassetsproduce(orareheldfortheproductionof)passiveincome(the“50%test”).Forthesepurposes,passiveincomegenerallyincludesinterest, dividends, annuities andother investment income. However, thePFICprovisions contain a look-throughrule under whicha non-U.S. corporation thatdirectlyorindirectlyownsatleast25%ofthevalueofthestockofanothercorporationgenerallyistreated,forpurposesofdeterminingwhetheritisaPFIC,asifitreceiveddirectlyitsproportionateshareoftheincome,andhelditsproportionateshareoftheassets,oftheothercorporation(the“look-throughrule”).Inaddition,pursuanttoaninsuranceexceptionthatwasamendedbythe2017Act,(a)passiveincomedoesnotincludeincomethataqualifyinginsurancecorporation(“QIC”)derives in the active conduct of an insurance business or incomeof a qualifying domestic insurance corporation (“QDIC”) (generally, a U.S. corporation withrespecttowhichthelook-throughruleappliesthatistaxableasaninsurancecompanyandissubjecttoU.S.federalincometaxonitsnetincome),and(b)passiveassetsdonotincludeassetsofaQICavailabletosatisfyliabilitiesoftheQICrelatedtoitsinsurancebusiness,iftheQICisengagedintheactiveconductofaninsurancebusiness,orassetsofaQDIC.

Generally, a non-U.S. corporation will be a QIC for a taxable year if it would be taxable as an insurance company if it were a U.S. corporation and itsapplicableinsuranceliabilities constitute morethan25%ofits total assets forataxableyear. Further, underrecentlyproposedregulations(the“2021ProposedRegulations”), aQICisinthe“activeconduct”ofaninsurancebusinessonlyifit satisfieseithera“factualrequirementstest”oran“activeconductpercentagetest.”ThefactualrequirementstestrequiresthattheofficersandemployeesoftheQICcarryoutsubstantialmanagerialandoperationalactivitiesonaregularandcontinuousbasiswithrespecttoitscorefunctionsandthattheyperformvirtuallyalloftheactivedecision-makingfunctionsrelevanttounderwritingfunctions.Theactiveconductpercentagetestgenerallyrequiresthat(i)thetotalcostsincurredbytheQICwithrespecttoitsofficersandemployeesforservicesrenderedwith respect to its core functions (other than investment activities) equal or exceed 50%of the total costs incurred by the QICwith respect to its officers andemployeesandanyotherpersonorentitiesforservicesrenderedwithrespecttoitscorefunctions(otherthaninvestmentactivities)and(ii)totheextenttheQICoutsourcesanypartofitscorefunctionstounrelatedentities,officersandemployeesoftheQICwithexperienceandrelevantexpertisemustselectandsupervisethepersonthatperformstheoutsourcedfunctions,establishobjectivesforperformanceoftheoutsourcedfunctionsandprescriberigorousguidelinesrelatingtotheoutsourcedfunctionswhichareroutinelyevaluatedandupdated.Undercertainexceptions,however,aQICthathasnooronlyanominalnumberofemployeesorthatisavehiclethathastheeffectofsecuritizingorcollateralizinginsurancerisksunderwrittenbyotherinsuranceorreinsurancecompaniesorisaninsurancelinked securities fund that invests in securitization vehicles generally is deemed not engaged in the active conduct of an insurance business. The officers andemployeesofcertainrelatedentitiesgenerallymaybetakenintoaccountforthesepurposes,providedthattheQICexercisesregularoversightandsupervisionovertheservicesperformedbytherelatedentity’sofficersandemployees.The2021ProposedRegulationswillnotbeeffectiveunlessanduntiladoptedinfinalform,buttaxpayersmayrelyonthemfortaxableyearsbeginningafterDecember31,2017iftheyareconsistentlyfollowed.

Webelievethat,basedontheimplementationofourcurrentbusinessplanandtheapplicationoftheinsuranceexception,ournon-U.S.insurancesubsidiariesshould be considered QICsengaged in the active conduct of an insurance business under one or both of the “factual requirements test” or the “active conductpercentagetest,”ourU.S.insurancesubsidiariesshouldbeconsideredQDICsandnoneoftheincomeorassetsofsuchinsurancesubsidiariesshouldbetreatedaspassive.Asaresult,basedontheapplicationofthelook-throughrule,webelievethatAspenHoldingsshouldnotbecharacterizedasaPFICforthecurrentyearortheforeseeablefuture.However,becauseoflegaluncertaintieswithrespecttotheinterpretationofthePFICrulesandwhetherthe2021ProposedRegulationswillbeadoptedasfinalregulationsintheircurrentform,andfactualuncertaintieswithrespecttoourplannedoperations,thereisariskthatAspenHoldingswillbecharacterized as a PFICinoneor more years. If AspenHoldingsis considereda PFIC, it couldhavematerial adverse taxconsequences for aninvestor that issubjecttoU.S.federalincometaxation.ProspectiveinvestorsshouldconsulttheirtaxadvisorsastotheeffectsofthePFICrules.

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U.S. tax-exempt organizations who own our shares may recognize unrelated business taxable income.

AU.S.tax-exemptorganizationgenerallywillrecognizeunrelatedbusinesstaxableincomeiftheorganizationisrequiredtoincludeingrossincomeanyofourinsuranceincomeundertheCFCrulesdescribedabove(includingtheRPIIprovisions).U.S.tax-exemptorganizationsareadvisedtoconsulttheirowntaxadvisorsregardingtheapplicabilityoftheserulestotheirownershipofourshares.

The impact of Bermuda’s letter of commitment to the OECD to eliminate harmful tax practices is uncertain and could adversely affect our tax status inBermuda.

The OECDhas published reports and launched a global dialogue among member and non-member countries on measures to limit harmful tax competition.Thesemeasuresarelargelydirectedatcounteractingtheeffectsoftaxhavensandpreferentialtaxregimesincountriesaroundtheworld.IntheOECD’sprogressreport dated April 2, 2009, Bermuda was designated as an OECD “White List” jurisdiction that has substantially implemented the internationally agreed taxstandards.ThestandardsfortheOECDcompliancearetohaveatleast12signedTaxInformationExchangeAgreements(“TIEAs”)withotherOECDmembersornon-OECDmembers.Bermudahassignedapproximately41TIEAswhichexceedstherequisiteamountanddemonstratesBermuda’scommitmenttopreservethestandards.InApril2016,BermudaagreedtoparticipateintheTaxSharingrequirementsforCBCR.

Bermudaremainscommittedtotaxtransparency,whichisevidencedbyadoptingeconomicsubstancelegislation,whichhasbeendeemedcompliantbytheE.U.andwasdesignedtoimplementtheworkoftheForumonHarmfulTaxPracticesunderAction5oftheOECD'sBEPSReports.AnychangesinthetaxlawofanOECDmemberstateorinresponsetoachangeinE.U.policies,couldsubjectustoadditionaltaxesandweareunabletopredictatthistimewhetheritwouldhaveamaterialadverseimpactonouroperationsandresults.

Changes to Bermuda tax policies may impact our financial position.

Under current Bermudalaw, weare not subject to taxonincome, profits, withholding, capital gains or capital transfers. Furthermore, weobtainedfromtheMinister of Finance of Bermuda under the Exempted Undertakings Tax Protection Act 1966 (as amended) an assurance that, in the event Bermuda enactslegislationimposingtaxcomputedonprofits, income,anycapital asset, gainorappreciation, oranytaxinthenatureofestatedutyorinheritancetax, thentheimpositionofthetaxwillnotbeapplicabletousorouroperationsuntilMarch31,2035.TaxpolicyandlegislationinBermudacouldchangeinthefuture(asisthecaseinotherjurisdictions)andassuchnoguaranteecanbegivenastowhetherthecurrenttaxtreatmentaffordedtouswillcontinueafterMarch31,2035.

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Item 4. Information on the Company

A. History and Development of the Company

AspenInsuranceHoldingsLimitedwasincorporatedonMay23,2002asaholdingcompanyheadquarteredinBermuda.Weunderwritespecialtyinsuranceandreinsurance on a global basis through our Operating Subsidiaries based in Bermuda, the United States and the United Kingdom. We also have branches inAustralia, Canada, Singapore andSwitzerland. Theprincipal office is located at 141Front Street, Hamilton, HM19, Bermuda(telephonenumber: +1441-295-8201).

OnFebruary15,2019,followingreceiptofregulatoryapprovals,theCompany’spubliclytradedordinaryshareswereacquiredbyHighlandsBermudaHoldco,Ltd.(formerlyknownasHighlandsHoldings,Ltd.)(“Parent”),aBermudaexemptedcompany,andanaffiliateofcertaininvestmentfundsmanagedbyaffiliatesofApolloGlobalManagement,Inc.,aleadingglobalinvestmentmanager(collectivelywithitssubsidiaries,“Apollo”).Asaresultoftheacquisition,theCompany’sordinarysharesarenolongertradedontheNewYorkStockExchange(the“NYSE”).TheCompany’spreferencesharesanddepositarysharescontinuetobelistedontheNYSEunderthefollowingsymbols:AHLPRC,AHLPRDandAHLPRE.Forinformationonthepreferencesharesandthedepositaryshares,refertoItem18,Note12ofourconsolidatedfinancialstatements,“CapitalStructure.”

During2020,wesoldtherenewalrightstooursuretyinsuranceoperationsaswellasourownershipinterestinthestrategicpartnershipthroughwhichvirtuallyall of our U.S. agriculture business was derived. For more information on these transactions, refer to Item 5 “Operating and Financial Review — RecentDevelopments—SaleofOwnershipInterestinCropRe.”andItem5“OperatingandFinancialReview—RecentDevelopments—SuretyInsuranceBusiness.”

TheCompanymaintainsawebsiteatwww.aspen.co.Theinformationonourwebsiteisnotincorporatedbyreferenceinthisreport.Wemakeavailable,freeofchargethroughourwebsite,ourAnnualReportsonForm20-FandotherreportsfiledorfurnishedpursuanttoSection13(a)or15(d)oftheExchangeActassoonasreasonablypracticableafterweelectronicallyfilesuchmaterialwith,orfurnishsuchmaterialto,theU.S.SecuritiesandExchangeCommission(“SEC”).

TheSECmaintainsaninternetsitethatcontainsreportsandotherinformationregardingissuers,includingtheCompany,thatfileelectronicallywiththeSEC.TheaddressoftheSEC’swebsiteiswww.sec.gov.

B. Business Overview

WeareaBermuda-basedholdingcompany,whoseprincipalbusinessismarketingandunderwritingspecialtyinsuranceandreinsuranceonaglobalbasis.Ourbusiness is comprised of: (i) underwriting operations, which includes our risk-bearing insurance and reinsurance operations; (ii) investing activities, which areprimarilyrelatedtoandsupportourunderwritingoperations;and(iii)ourAspenCapitalMarketsoperations,whichearnsmanagementandperformancefeesfromtheCompanyandotherthird-partyinvestorsprimarilythroughthemanagementofinsurancelinkedsecurities(“ILS”)fundsandotherofferings.Wemanageourunderwritingoperationsastwodistinctbusinesssegments,AspenInsuranceandAspenReinsurance(“AspenRe”),toenhanceandbetterserveourglobalcustomerbase.FinancialdatarelatingtoourtwobusinesssegmentsisincludedinItem5,“OperatingandFinancialReviewandProspects”andinItem18,Note3ofourconsolidatedfinancialstatements,“SegmentReporting.”

Aspen Reinsurance.

AspenReprovidesreinsurancetocedingcompanies,alsoreferredtoascedantsorreinsureds.AspenRe’sofferingsinclude,butarenotlimitedto(i)propertycatastrophe reinsurance, (ii) other property reinsurance, (iii) casualty reinsurance, and (iv) specialty reinsurance. We offer reinsurance on both a treaty andfacultativebasis,andonbothaproportional(orquotashare)andnon-proportional(orexcessofloss)basis.

Ourreinsurancebusinessis sourcedprincipallythroughbrokersandreinsuranceintermediaries, withwhomweaimtomaintainstrongrelationships, havingbecomeavaluedriskmanagementpartnertotheleadinginsurerswithwhomwedobusiness.WewritevariousexcessoflosscontractsandproportionaltreatiesthroughAspenBermuda,aClass4insurerincorporatedunderthelawsofBermuda,andlicensedundertheInsuranceactof1978ofBermudaasamended(the“InsuranceAct”).AspenBermudamaintainsbranchofficesinSwitzerlandandSingapore.Theexcessoflosscontractsareprincipallypropertycatastrophepoliciesreinsuringnon-affiliatedinsurerslocatedmainlyintheUnitedStates,Europe,andAsiaPacific.Theproportionaltreatiesprincipallycoverpropertyrisksreinsuringnon-affiliatedinsurerslocatedintheUnitedStates,Europe,andAsiaPacific.Wewritepropertycatastrophe,property,casualtyandspecialtyreinsurancebusinessthroughAspenU.K.and

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its branches in Canada, Singapore, and Australia. Syndicate 4711 is managed by AMALand AULis the corporate member. We also access Lloyd’s Brusselsthrough Lloyd’s Insurance Company, S.A. stamp 5383. Since 2017, AAIC also underwrote crop reinsurance business in the United States through a strategicpartnershipwithCGBDiversifiedServices,Inc.(“CGBDS”).OnDecember14,2020,wesoldourownershipinterestinthestrategicpartnership.ThesaleislikelytoresultinamaterialdiminutionofourU.S.agriculturalbusinessin2021andbeyond.FormoreinformationonCGBDS,referto“—SpecialtyReinsurance”andItem5“OperatingandFinancialReview—RecentDevelopments—SaleofOwnershipInterestinCropRe.”below.

Aspen Insurance

Ourinsurancesegmentoffersavarietyofinsuranceproductsconsistingof(i)propertyandcasualtyinsurance,(ii)marine,aviationandenergyinsurance,and(iii)andfinancialandprofessionallinesinsurance.Inourinsurancesegment,theseproductsarewrittenintheLondonMarketprimarilybyAspenU.K.andviatheLloyd’splatformand,intheUnitedStates,byAAICandAspenSpecialty(onanadmittedandexcessandsurpluslinesbasis,respectively).Wealsowritecasualtyand financial and professional lines business through Aspen Bermuda and financial and professional lines business in the Asia Pacific region through AspenSingaporePte.Ltd.(“AspenSingapore”),whichbindsbusinessforSyndicate4711.

Investments

Ourinvestmentoperationsseektodeliverstableinvestmentincomeandtotalreturnthroughallmarketcycleswhilemaintainingappropriateportfolioliquidityandcreditqualitytomeettherequirementsofourcustomers,ratingagenciesandregulators.Incomefromourinvestmentoperationsisincludedincorporateandotherincomeandexpense.Wedonotallocateourinvestedassetsbybusinesssegmentasweevaluateunderwritingresultsofeachbusinesssegmentseparatelyfromtheresultsofourinvestmentportfolio.

Aspen Capital Markets

WeparticipateinthealternativereinsurancemarketthroughAspenCapitalMarkets,whichfocusesondevelopingalternativereinsurancestructurestoleveragethe Company’s existing underwriting franchise, increase its operational flexibility in the capital markets andprovide investors direct access to its underwritingexpertise.AspenCapitalMarketsleveragestheCompany’sunderwritingandanalyticalexpertiseandearnsmanagementandperformancefeesfromtheCompanyandotherthird-partyinvestorsprimarilythroughthemanagementofILSfundsandotherofferings.Itoperatestwodistinctstrategies,namely,buildinginsurancerisk portfolios tailored to investor objectives through managed funds such as Aspen Cat Fund Limited, and structuring and placing a defined Aspen portfolioaligned with capital markets investors through the use of sidecars, including Peregrine Reinsurance Ltd. (“Peregrine”), a single purpose insurer. For moreinformationonPeregrine,see“RegulatoryMatters-Bermuda-PeregrineandSilverton”below.

IncomefromAspenCapital Markets’ activities is primarily allocated to the line of business being cededand serves to reduce acquisition expenses for thatbusiness.WhileAspenCapitalMarketshashistoricallyfocusedonpropertycatastrophebusiness,inrecentyears,ithasexpandedtoprovidecapacityforpropertyinsuranceandreinsurance,specialtyreinsuranceandcasualtyinsuranceandreinsurance.

Business Segments

We have determined our reportable segments, Aspen Re (“Reinsurance”) and Aspen Insurance (“Insurance”), by taking into account the manner in whichmanagementmakesoperatingdecisionsandassessesoperatingperformance.Profitorlossforeachofthebusinesssegmentsismeasuredbyunderwritingprofitorloss. Underwriting profit is the excess of net earned premiumsover the sumof losses and loss expenses, amortization of deferred policy acquisition costs andgeneralandadministrativeexpenses.Underwritingprofitorlossprovidesabasisformanagementtoevaluatethesegment’sunderwritingperformance.

Managementmeasuressegmentresultsonthebasisofthecombinedratio,whichisobtainedbydividingthesumofthelossesandlossexpenses,amortizationof deferred policy acquisition costs and operating and administrative expenses by net earned premiums. Other than corporate expenses, indirect operating andadministrativeexpensesareallocatedtobusinesssegmentspredominantlybasedoneachsegment’sproportionalshareofgrossearnedpremiums.

We provide additional disclosures for corporate and other (non-operating) income and expenses. Corporate and other income and expenses include netinvestmentincome,netrealizedandunrealizedinvestmentgainsorlosses,expensesassociatedwithmanagingtheAspenGroup,certainstrategicandothercosts,changesinfairvalueofderivativesorloannotesissuedbyvariableinterestentities,interestexpenses,netrealizedandunrealizedforeignexchangegainsorlosses,andincometaxes,

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whicharenotallocatedtothebusinesssegments.Corporateexpensesarenotallocatedtoourbusinesssegmentsastheytypicallydonotfluctuatewiththelevelsofpremiumswrittenandarenotdirectlyrelatedtooursegmentoperations.Wedonotallocateourassetsbybusinesssegmentasweevaluateunderwritingresultsofeach business segment separately from the results of our investment portfolio. Segment profit or loss for each of our business segments is measured byunderwritingprofitorloss.

ThetablebelowsetsforththegrosswrittenpremiumsbybusinesssegmentforthetwelvemonthsendedDecember31,2020,2019and2018:

Twelve Months Ended December 31,2020

Twelve Months Ended December 31,2019

Twelve Months Ended December 31,2018

Business Segment

Gross Written

Premiums % of Total

Gross Written

Premiums % of Total

Gross Written

Premiums % of Total ($ in millions, except for percentages)Reinsurance $ 1,660.8 44.8 % $ 1,485.5 43.2 % $ 1,495.7 43.4 %Insurance 2,042.8 55.2 1,956.9 56.8 1,951.2 56.6Total $ 3,703.6 100.0 % $ 3,442.4 100.0 % $ 3,446.9 100.0 %

Forareviewofourresultsbybusinesssegment,refertoItem5,“OperatingandFinancialReviewandProspects”andItem18,Note3ofourconsolidatedfinancialstatements,“SegmentReporting.”

Reinsurance

Thereinsurancebusinesswewritecanbeanalyzedbygeographicregion,reflectingthelocationofthereinsuredrisks,assetforthinthetablebelowforthetwelvemonthsendedDecember31,2020,2019and2018:

Twelve Months Ended December 31,

2020Twelve Months Ended December 31,

2019Twelve Months Ended December 31,

2018

Reinsurance

GrossWritten

Premiums % of Total

Gross Written

Premiums % of Total

GrossWritten

Premiums % of Total ($ in millions, except for percentages)Australia/Asia $ 180.0 10.8 % $ 139.5 9.4 % $ 141.3 9.4 %Caribbean 3.4 0.2 5.2 0.4 3.7 0.2Europe(excludingU.K.) 73.5 4.4 69.2 4.7 75.0 5.0UnitedKingdom 9.4 0.6 15.1 1.0 9.2 0.6UnitedStates&Canada 870.9 52.4 770.3 51.8 741.2 49.7WorldwideexcludingUnitedStates 21.7 1.3 21.0 1.4 33.9 2.3WorldwideincludingUnitedStates 425.0 25.6 371.8 25.0 387.8 25.9Others 76.9 4.7 93.4 6.3 103.6 6.9Total $ 1,660.8 100.0 % $ 1,485.5 100.0 % $ 1,495.7 100.0 %

_______________(1)“UnitedStatesandCanada”consistsofindividualpoliciesthatinsurerisksspecificallyintheUnitedStatesand/orCanada,butnotelsewhere.Italsoincludes

gross written premium of $334.8 million related to CGB Diversified Services, Inc. (“CGB DS”); (2019 — $312.5 million (CGB DS); (2018 —$259.7millionrelatedtoCGBDSand$33.1millionrelatedtoAGLogicHoldings,LLCanditsaffiliates(“AgriLogic”)whichwepurchasedinJanuary2016andsoldinDecember2017)aspartofourstrategicpartnershipwithCGBDS).FormoreinformationonCGBDS,referto“—SpecialtyReinsurance”below.

(2)“WorldwideexcludingtheUnitedStates”consistsofindividualpoliciesthatinsureriskswherevertheymaybeacrosstheworldbutspecificallyexcludestheUnitedStates.

(3)“WorldwideincludingtheUnitedStates”consistsofindividualpoliciesthatinsureriskswherevertheymaybeacrosstheworldbutspecificallyincludestheUnitedStates.

(1)

(2)

(3)

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AspenRe’sgrosswrittenpremiumsbyprincipallineofbusinesswereasfollowsforthetwelvemonthsendedDecember31,2020,2019and2018:

Twelve Months Ended December 31,

2020Twelve Months Ended December 31,

2019Twelve Months Ended December 31,

2018

Reinsurance

GrossWritten

Premiums % of Total

Gross Written

Premiums % of Total

GrossWritten

Premiums % of Total ($ in millions, except for percentages)Propertycatastrophereinsurance $ 312.0 18.8 % $ 249.6 16.8 % $ 262.8 17.6 %Otherpropertyreinsurance 399.8 24.1 356.9 24.0 346.0 23.1Casualtyreinsurance 394.4 23.7 294.7 19.8 328.1 21.9Specialtyreinsurance 554.6 33.4 584.3 39.4 558.8 37.4Total $ 1,660.8 100.0 % $ 1,485.5 100.0 % $ 1,495.7 100.0 %

`1

_______________(1)Includesgrosswrittenpremiumof$334.8millionrelatedtoCGBDS;(2019—$312.5million(CGBDS);(2018—$259.7million(CGBDS);$33.1million

(AgriLogic).

Property Catastrophe Reinsurance:Property catastrophereinsurance is generally writtenona treaty excess of loss basis whereweprovideprotectiontoaninsurerforanagreedportionofthetotallossesfromasingleeventinexcessofaspecifiedlossamount.Intheeventofaloss,mostcontractsprovideforcoverageofasecondoccurrencefollowingthepaymentofapremiumtoreinstate thecoverageunderthecontract, whichis referredtoasareinstatement premium.Thecoverageprovidedunderexcessoflossreinsurancecontractsmaybeonaworldwidebasisorlimitedinscopetoselectedregionsorgeographicalareas.

Other Property Reinsurance:Otherpropertyreinsuranceincludespropertyriskswrittenonexcessoflossandproportional treaties, facultativeorsingleriskreinsurance.Riskexcessoflossreinsuranceprovidescoveragetoareinsuredwhereitexperiencesalossinexcessofitsretentionlevelonasingle“risk”basis.A“risk”inthiscontextmightmeantheinsurancecoverageononebuildingoragroupofbuildingsforfireorexplosionortheinsurancecoverageunderasinglepolicywhichthereinsuredtreatsasasinglerisk.Thislineofbusinessisgenerallylessexposedtoaccumulationsofexposuresandlossesbutcanstillbeimpactedbycatastrophes,suchasearthquakesandhurricanes.Proportionaltreatyreinsuranceprovidesproportionalcoveragetothereinsured,meaningthat,subjecttoeventlimitswhereapplicableandcedingcommissions,wepaythesameshareofthecoveredoriginallossesaswereceiveinpremiumschargedforthecoveredrisks.Proportionalcontractstypicallyinvolvecloseclientrelationshipswhichoftenincluderegularauditsofthecedants’data.

Casualty Reinsurance:Casualtyreinsuranceiswrittenonanexcessofloss,proportionalandfacultativebasisandconsistsofU.S.treaty,internationaltreatyand casualty facultative reinsurance. Our U.S. treaty and facultative business comprises exposures to workers’ compensation (including catastrophe), medicalmalpractice, general liability, auto liability, professional liability and excess liability including umbrella liability. Our international treaty business reinsuresexposuresmainlywithrespecttogeneralliability,autoliability,professionalliability,workers’compensationandexcessliability.

Specialty Reinsurance:Specialtyreinsuranceiswrittenonanexcessoflossandproportionalbasisandconsistedofcreditandsuretyreinsurance,agriculturereinsurance, mortgage reinsurance and insurance, marine, aviation, terrorism, engineering, cyber and other specialty lines. Our credit and surety reinsurancebusinessconsistsoftradecredit,surety(mainlyEuropean,JapaneseandLatinAmericanrisks)andmortgagereinsuranceandinsuranceandpoliticalrisks.In2019,weceasedwritingcreditandsuretyreinsuranceandsoldourrenewalrightstothatbookofbusinesstoathirdparty.Themortgagereinsuranceandinsuranceonpolitical riskswasnot includedinthetransactionandwecontinueto underwrite this coverage. Ourspecialty agricultural reinsurance business covers cropandmulti-peril business. Other specialty lines include reinsurance treaties andsomeinsurance policies covering policyholders’ interests in marine, energy, aviationliability,space,contingency,terrorism,engineering,nuclearandpersonalaccident.

Inaddition,specialtyreinsuranceincludedU.S.cropinsurancebusinesswrittenonareinsurancebasisthroughourstrategicpartnershipwithCGBDSviaCropRe Services LLC (“Crop Re”), a Delaware limited liability company responsible for directing the placement of reinsurance on behalf of CGB DS and CGBInsuranceCompany(“CGBIC”),anIndianainsurancecompanyaffiliateofCGBDSandanRMAlicensedcropinsurer.WealsowriteasmallamountofadmittedprimaryU.S.cropinsurance.InSeptember2020,wereceivednoticefromCGBDSthatitscontrollingparententeredintoadefinitiveagreementforthesaleofCGBDStoathirdparty.ThesaleofCGBDStriggeredanoptionforCGBDStopurchaseAspen’s23.2%ownershipinterestinCropRe.CGBDSexercisedthisrightandpurchasedAspen’sinterestinCropReonDecember14,2020(the“CGBSale”).TheCGBSaleislikelytoresultinamaterialdiminutionofourU.S.agriculturalbusinessin2021and

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beyond.FormoreinformationontheCGBSale,refertoItem5“OperatingandFinancialReview—RecentDevelopments—SaleofOwnershipInterestinCropRe.”

Ahighpercentageofthepropertycatastrophereinsurancecontractswewriteexcludeorlimitcoverageforlossesarisingfromtheperilofterrorism.WithintheU.S.,ourotherpropertyreinsurancecontractsgenerallyincludelimitedcoverageforactsthatarecertifiedas“actsofterrorism”bytheU.S.TreasuryDepartmentundertheTerrorismRiskInsuranceAct(includingitsvariousextensions,“TRIA”).Wehavewrittenalimitednumberofpropertyreinsurancecontracts,bothonapro rata and excess of loss basis, specifically covering the peril of terrorism. These contracts typically exclude coverage for nuclear, biological, chemical orradiologicalattack,thoughwehavewrittenasmallnumberofcontractsthatdonotexcludecoverageforsuchattacks,thecoverageofwhichmaybeapplicabletonon-terrorismevents.

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Insurance

Theinsurancebusinesswewritecanbeanalyzedbygeographicregion,reflectingthelocationoftheinsuredrisk,assetforthinthetablebelowforthetwelvemonthsendedDecember31,2020,2019and2018:

Twelve Months Ended December 31,

2020Twelve Months Ended December 31,

2019Twelve Months Ended December 31,

2018

Insurance

GrossWritten

Premiums % of Total

Gross Written

Premiums % of Total

GrossWritten

Premiums % of Total ($ in millions, except for percentages)Australia/Asia $ 71.2 3.5% $ 76.4 3.9 % $ 34.6 1.8 %Caribbean 2.5 0.1 4.1 0.2 4.0 0.2Europe(excludingU.K.) 59.5 2.9 13.6 0.7 17.6 0.9UnitedKingdom 233.7 11.4 280.6 14.3 280.9 14.4UnitedStates&Canada 1,372.0 67.2 1,233.6 63.1 1,134.7 58.1WorldwideexcludingUnitedStates 1.4 0.1 42.0 2.1 36.2 1.9WorldwideincludingUnitedStates 208.4 10.2 243.1 12.4 388.0 19.9Others 94.1 4.6 63.5 3.3 55.2 2.8Total $ 2,042.8 100.0 % $ 1,956.9 100.0 % $ 1,951.2 100.0 %

_______________(1)“UnitedStatesandCanada”consistsofindividualpoliciesthatinsurerisksspecificallyintheUnitedStatesand/orCanada,butnotelsewhere.(2)“WorldwideexcludingtheUnitedStates”consistsofindividualpoliciesthatinsureriskswherevertheymaybeacrosstheworldbutspecificallyexcludesthe

UnitedStates.

(3)“WorldwideincludingtheUnitedStates”consistsofindividualpoliciesthatinsureriskswherevertheymaybeacrosstheworldbutspecificallyincludestheUnitedStates.

OurgrosswrittenpremiumsbyourprincipallineofbusinesswithinourinsurancesegmentwereasfollowsforthetwelvemonthsendedDecember31,2020,2019and2018:

Twelve Months Ended December 31,

2020Twelve Months Ended December 31,

2019Twelve Months Ended December 31,

2018

Insurance

GrossWritten

Premiums % of Total

Gross Written

Premiums % of Total

GrossWritten

Premiums % of Total ($ in millions, except for percentages)Propertyandcasualtyinsurance $ 942.5 46.1 % $ 861.2 44.0 % $ 903.9 46.3 %Marine,aviationandenergyinsurance 224.4 11.0 301.7 15.4 368.4 18.9Financialandprofessionallinesinsurance 875.9 42.9 794.0 40.6 678.9 34.8Total $ 2,042.8 100.0 % $ 1,956.9 100.0 % $ 1,951.2 100.0 %

Property and Casualty Insurance:ThepropertyandcasualtyinsurancelineconsistsofU.S.andU.K.commercialproperty,commercialliability,U.S.primarycasualty,excesscasualty,environmentalliabilityandrailroadliability,writtenonaprimary,excess,quotashare,programandfacultativebasis.

U.S. and U.K. Commercial Property: Propertyinsuranceprovidesphysicaldamageandbusinessinterruptioncoverageforlossesarisingfromweather,fire,theftandothercauses. TheU.S.commercialpropertyteamcoversmercantile,manufacturing,municipalandcommercialrealestatebusiness.TheU.K.commercialteam’sclientbaseispredominantlyU.K.institutionalpropertyowners,smallandmiddlemarketcorporatesandpublicsectorclients.

Commercial Liability: Commercial liability is primarily written in the United Kingdomandprovides employers’ liability coverage, products and publicliabilitycoverageforinsuredsdomiciledintheUnitedKingdomandIreland.TheU.K.regionalteamalsocoversdirectors’andofficers’(“D&O”)andprofessionalindemnity,predominantlytosmallandmediumcorporates.ThemajorityofthisU.K.regionalD&OandprofessionalindemnitycoveragewasboundthroughanagencyagreementwithAspenRiskManagementLimited(“ARML”).InJuly2019,weplacedthebusinessboundbyARMLintorunoff.

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U.S. Primary Casualty: The U.S. primary casualty account consists primarily of lines written within the primary insurance sectors. We are focused ondeliveringexpertisetobrokersandcustomersinhospitality,realestate,constructionandproductsliability.

Excess Casualty:Theexcesscasualtylinecomprisesmediumandlarge,sophisticatedandrisk-managedinsuredsworldwideandcoversbroad-basedrisksatlead/highexcessattachmentpoints,includinggeneralliability,commercialandresidentialconstructionliability,lifescience,railroads,trucking,productandpublicliabilityandassociatedtypesofcoverfoundingeneralliabilitypoliciesintheglobalinsurancemarket,writtenfromtheUnitedKingdom,theUnitedStatesandBermuda.

Environmental Liability:Theenvironmentalaccountprimarilyprovidescontractors’pollutionliabilityandpollutionlegalliabilityacrossindustrysegmentsthathaveenvironmentalregulatorydriversandcontractualrequirementsforcoverage,includingrealestateandpublicentities,contractorsandengineers,energycontractorsandenvironmentalcontractorsandconsultants.ThebusinessiswritteninboththeprimaryandexcessinsurancemarketsintheUnitedStates,CanadaandtheUnitedKingdom.

Railroad Liability: Our railroad liability business consists of primary andexcess liability business for freight, commuter andexcursion railroads. It alsoprovidesgeneralliabilitycoveragetotherailroadsupportindustry(contractors,repairshopsandproductsmanufacturers)aswellascontingentliabilityforrailcarfleetowners/managersandrailroadprotectiveliabilityintheUnitedStates.

Ona significant portion of our property and casualty insurance contracts we are obligated to offer terrorismcoverage under TRIA. Wherever possible, weexcludecoverageprotectionagainstnuclear,biological,chemicalorradiological(“NBCR”)attacks.However,certainU.S.states(notablyNewYorkandFlorida)prohibitadmittedinsurancecompanies,suchasAAIC,fromfullyexcludingsuchperils,resultinginsomelevelofexposurestoNBCRaswellasfirefollowingsuchevents.WewouldexpecttobenefitfromtheprotectionofTRIAandtheover-arching$100billionindustrylosscap(subjecttotherelevantdeductibleandco-retention).

Marine, Aviation and Energy Insurance:Our marine, aviation and energy insurance line consists of marine and energy liability, onshore energy physicaldamage,offshoreenergyphysicaldamage,marinehull, specieandinlandandoceanmarine, writtenonaprimary, excess, quotashare, programandfacultativebasis.

Marine and Energy Liability:InFebruary2020,wedeterminedtoceasewritingmarineandenergyliabilitybusinessandthebusinesswasputintorunoff.Priortothat,themarineandenergyliabilitybusinesswasbasedintheU.K.andincludedmarineliabilitycovermainlyrelatedtotheliabilitiesofship-ownersandportoperators,includingreinsuranceofProtectionandIndemnityClubs.Italsoprovidedliabilitycoverglobally(includingtheU.S.)forcompaniesintheoilandgassector,bothonshoreandoffshoreandinthepowergenerationsector.ThisclassalsoincludedcommercialconstructionliabilityforU.S.companiesintheoilandgassector,whichisnowbeingwrittenunderourglobalexcesscasualtyline.

Onshore Energy Physical Damage: Ourmarine,energyandconstructionpropertyunitunderwritesavarietyofworldwideonshoreenergyandconstructionsectorclassesofbusinesswithafocusonpropertycovers.

OffshoreEnergy Physical Damage:Offshoreenergyphysicaldamageprovidesinsurancecoveragainstphysicaldamagelossesinadditiontooperators’extraexpensesforcompaniesoperatingintheoilandgasexplorationandproductionsector.

Marine Hull:Themarinehullteaminsuresphysicaldamagetoships(includingwarandassociatedperils)andrelatedmarineassets.EffectiveAugust2018,weceasedunderwritingmarinehullontheLloyd’splatformalthoughwecontinuetowritehull-relatedrisksinourU.S.oceanmarinebusiness.

Specie:Thespeciebusinesslinefocusesontheinsuranceofhighvaluepropertyitemsonanallrisksbasis,includingfineart,generalandbankrelatedspecie,jewelers’blockandarmoredcar.

Inland and Ocean Marine: Theinlandandoceanmarineteamwritesbusinessprincipallycoveringbuilders’constructionrisk,contractors’equipment,andglobaltransportationexposuressuchasmarinecargoandhull,inlandtransit,warehousingandwar,inadditiontoexhibition,fineartsandmuseumsinsurance.Thebookalso includes business generated by our subsidiary, Blue Waters Insurers, Corp., which acts as our managing general agent in Puerto Rico and producesinland,oceanmarineandcargobusinessinPuertoRico.

Aviation:InAugust2018,wedecidedtonolongerunderwriteaviationbusiness.PriortoAugust2018,theaviationteamwrotephysicaldamageinsuranceonhulls andspares (including war andassociated perils), aviation hull deductible cover andcomprehensive legal liability for airlines, smaller operators of airlineequipment,airportsandassociatedbusinessandnon-criticalcomponentpartmanufacturers.

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Financial and Professional Lines Insurance:Ourfinancialandprofessionallinesconsistsoffinancialandcorporaterisks,professionalliability,managementliability,creditandpoliticalrisks,crisismanagement,accidentandhealth,suretyrisks,andcyberliability,writtenonaprimary,excess,quotashare,programandfacultativebasis.

Financial and Corporate Risks:Ourfinancialinstitutionsbusinessiswrittenonbothaprimaryandexcessoflossbasisandconsistsofprofessionalliability,crimeinsuranceandD&Ocover,withthelargestexposurecomprisingrisksheadquarteredintheUnitedKingdom,followedbyAustralia,theUnitedStatesandCanada.Wecoverfinancialinstitutionsincludingcommercialandinvestmentbanks,assetmanagers,insurancecompanies,stockbrokersandinsuredswithhybridbusiness models. This account also includes a bookof D&Oinsurance for commercial insureds located outside of the United States and a worldwide book ofrepresentationsandwarrantiesandtaxindemnitybusiness.

Professional Liability:OurprofessionalliabilitybusinessiswrittenoutoftheUnitedStates(includingerrorsandomissions(“E&O”)),theUnitedKingdomandBermudaandiswrittenonbothaprimaryandexcessoflossbasis.Weinsureawiderangeofprofessionsincludinglawyers,accountants,architects,engineers,doctorsandmedicaltechnicians.Thisaccountmayalsoextendcoverageforcyberliabilityanddataprotectioninsurance.Thecyberliabilityanddataprotectioninsurancecovers firmsfor first party costs andthird-party liabilities associated withcybersecurity breachandbreachof contractual or statutorydata protectionobligations.

Management Liability: OurmanagementliabilitybusinessiswrittenoutoftheUnitedStates,theUnitedKingdomandBermuda.Weinsureadiversegroupofcommercial andfinancial institutions predominantly onanexcess basis. Our products include D&Oliability, fiduciary liability, employment practices liability,fidelityinsuranceandblendedliabilityprogramsincludingE&Oliability. ThefocusoftheaccountispredominantlyonrisksheadquarteredintheU.S.orriskswithamaterialU.S.exposure.

Credit and Political Risks:Thecreditandpoliticalrisksteamwritesbusinesscoveringthecreditandcontractfrustrationrisksonavarietyoftradeandnon-traderelatedtransactions,aswellaspoliticalrisks(includingmulti-yearwaronlandcover).Weprovidecreditandpoliticalriskscoverworldwidebutwithconcentrationsinanumberofcountries,suchasChina,Brazil,theNetherlandsandtheUnitedStates.

Crisis Management: TheCrisisManagementteamwritesinsurancedesignedtoprotectindividualsandcorporationsoperatinginhigh-riskareasaroundtheworld, including covering the shipping industry’s exposure to acts of piracy. It also writes terrorism and political violence insurance, providing coverage fordamagetoproperty(largelyfixedassetssuchasbuildings)resultingfromactsofterrorism,strikes,riots,civilcommotionorpoliticalviolence.Thisbookiswrittenon a global basis, although capacity is selectively deployed. Also included in Crisis Management is our U.S. food and beverage product recall business. InDecember2020,wesoldtherenewalrightstotheU.S.productrecallbusinesstoathirdparty.

Accident and Health:InMarch2020,wedeterminedtoexitourglobalaccidentandhealthlineofbusinessandbeganwindingdownthebusiness.Priortothat, the global accident and health team focused on insurance and reinsurance products which help protect individuals, groups and companies from theconsequences of accidental death or disability whether resulting from accident or sickness. This may include single or multi-person losses as well as majorcatastrophiceventssuchasaircrashes,earthquakesorterroristattacks.Coveragewrittenincludeswholeaccounttreatyandfacultativereinsuranceprotectionforinsurancecompanies.

Surety Risks:Oursuretyteamwritescommercialsuretyrisks,admiraltybondsandsimilarmaritimeundertakingsincluding,butnotlimitedto,federalandpublicofficialbonds,licenseandpermitsandfiduciaryandmiscellaneousbonds,focusedonFortune1000companiesandlarge,privatelyownedcompaniesinthe United States. In July 2020, we sold our renewal rights to our surety insurance book of business to a third party and executed a loss portfolio transfertransactionforthetransferofprior-yearliabilities.Wecurrentlycontinuetounderwriteonlyasmallportionofsuretybusinessonafrontedbasistothepurchaserinarenewalrightstransaction,whichissubjecttoa100%quotasharereinsuranceagreementbacktothepurchaser,orviaalimitedreinsurancequotashareofthebook.

Cyber Liability: Thisaccountiswrittengloballyandconsistsofourprivacyandnetworksecurityliability(cyberliability) productsaswell astechnologyliability.Ourprivacyandnetworksecurityliabilityproductsprovidefirstpartycostsandthird-partyliabilitiesassociatedwithprivacyandcybersecuritybreaches.Our technology liability product provides coverage for technology, media and telecommunications firms offering protection for damages and legal defenseexpensesassociatedwithfinanciallossclaimsfromthirdpartiesandvariousformsofintellectualpropertybreaches.Wealsoincorporatedataprotectionindemnityinsuranceagainstcostsandliabilitiesthatmayarisewhenacompanybreachesitsdataprotectionobligations.

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Underwriting and Reinsurance Purchasing

Ourobjective is to create a diversified portfolio of insurance and reinsurance risks, spread across lines of business, products, geographic areas of coverage,cedants and sources. The acceptance of appropriately priced risk is the core of our business. Underwriting requires judgment, based on important assumptionsabout matters that are inherently unpredictable andbeyondour control, andfor whichhistorical experience andprobability analysis maynot providesufficientguidance.Weviewunderwritingqualityandriskmanagementascriticaltooursuccess.

Underwriting. Weunderwriteaccordingtothefollowingprinciples:

• strive to build a diverse portfolio of risk that generates attractive returns by deploying capital in a targeted and efficient manner to deliver enhancedunderwritingprofitability;

• operatewithinagreedboundariesasdefinedbythebusinessplanfortherelevantclassofbusiness;

• operatewithinprescribedmaximumunderwritingauthoritylimits,whichwedelegatetoindividualunderwritersinaccordancewithanunderstandingofeachindividualunderwriter’scapabilities,tailoredtotheclassesofbusinesswrittenbytheparticularunderwriter;

• evaluatetheunderlyingdataprovidedbyclientsandadjustsuchdatawherewebelieveitdoesnotadequatelyreflecttheunderlyingexposure;

• price each submission based on our experience in the class of business, and where appropriate, by deploying one or more actuarial models eitherdevelopedinternallyorlicensedfromthird-partyproviders;

• maintainapeerreviewprocesstosustainhighstandardsofunderwritingdisciplineandconsistencyandasamplingmethodologyforsimplerinsurancerisks;

• engageinpeerreviewsformorecomplexriskbyseveralunderwritersandinputfromcatastropheriskmanagementspecialists,ourteamofactuariesandseniormanagement;and

• referrisksoutsideofagreedunderwritingauthoritylimitstotheGroupChiefExecutiveOfficerand/ortotheappropriateentityboardasexceptionsforapprovalbeforeweaccepttherisks.

Reinsurance Purchasing.Wepurchasereinsuranceandretrocessiontomitigateanddiversifyourriskexposuretoalevelconsistentwithourriskappetiteandtoincreaseourinsuranceandreinsuranceunderwritingcapacity.Theseagreementsprovideforrecoveryofaportionofourlossesandlossadjustmentexpensesfromourreinsurers.Theamountandtypeofreinsurancethatwepurchasevariesfromyeartoyearandisdependentonavarietyoffactors,including,butnotlimitedto,the cost of a particular reinsurance contract and the nature of our gross exposures assumed, with the aim of securing cost-effective protection. We have acentralizedcededreinsurancedepartmentwhichcoordinatestheplacementofallofourtreatyreinsuranceplacements.

Wehavereinsurancecoversinplaceforthemajorityofourinsuranceclassesofbusinessonanexcess-of-lossbasisand/orproportionaltreatybasis.Theexcessoflosscoversprovideprotectioninvariouslayersandexcessofvaryingattachmentpointsaccordingtothescopeofcoverprovided.

With respect to natural perils coverage, we buy protections that cover both our insurance and reinsurance lines of business through a variety of products,including,butnotlimitedto,excessoflossreinsurance,facultativereinsurance,aggregatecovers,wholeaccountcoversandcollateralizedproductswhichcanbeoneitheranindemnityoranindexlinkedbasis.Forexample,wemaypurchaseindustrylosswarrantyreinsurancewhichprovidesretrocessionalcoveragewheninsuranceindustrylossesforadefinedeventexceedacertainlevel.Weexpectthetypeandlevelofcoveragethatwepurchasewillvaryovertime,reflectingourviewofthechangingdynamicsoftheunderlyingexposureandthereinsurancemarkets.Wemanageourriskbyseekingtolimittheamountofexposureassumedfromanyonereinsuredandtheamountoftheaggregateexposuretocatastrophelossesfromasingleeventinanyonegeographicalzone.Additionally,AspenRecontinues to purchase quota share andretrocessional reinsurance protection for a rangeof international perils andworldwidecatastrophe losses throughAspenCapitalMarketsandothercollateralizedreinsurancearrangements.

Althoughreinsuranceagreementscontractuallyobligateourreinsurerstoreimburseusforanagreed-uponportionofourgrosspaidlosses,weremainliabletoourinsuredstotheextentthatourreinsurersdonotmeettheirobligationsundertheseagreements.Asaresult,andinlinewithourriskmanagementobjectives,weevaluatethefinancialconditionofourreinsurersandmonitorconcentrationsofcreditriskonanon-goingbasis.Ingeneral,weseektoplaceourreinsurancewithhighly rated companies with which we have a strong trading relationship or have fully collateralized arrangements in place. We maintain a list of authorizedreinsurersgradedforshort,mediumandlongtailbusinesswhichisregularlyreviewedandupdated.

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TheCompanyhasenteredintoanadversedevelopmentcoverreinsuranceagreementwithasubsidiaryofEnstarGroupLimited(“Enstar”),pursuanttowhichEnstar's subsidiary will reinsure losses incurred on or prior to December 31, 2019. Enstar’s subsidiary will provide $770 million of cover in excess of $3.805billionretentionuptoanaggregatelimitof$4.575billion,andanadditional$250millionofcoverinexcessof$4.815billion.Theconsiderationforthisagreementis$770.0millionplusinterestat3.75%perannum,compoundingdaily,fromtheeffectivedateJanuary1,2020totheclosingdate.ThetransactionclosedinJune2020followingreceiptoftherequiredregulatoryapprovals.WeexpecttheADCtoreducevolatilityfromourhistoricalbusinessgoingforward.

Foradditionalinformation,refertoItem18,Note7ofourconsolidatedfinancialstatements,“Reinsurance”

Risk Management

Wehaveacomprehensiveriskmanagementframeworkthatdefinesthecorporateriskappetite,riskstrategyandthepoliciesinplacetomonitor,manageandmitigatetheriskinherentinourbusiness.Ourriskmanagementframeworkcoversall risksinourriskuniverse,onacurrentandforwardlookingbasis,andisimplementedinaconsistentmanneracrosstheAspenGroup.Itisthebasisthroughwhichweprotectourfranchisevalueandseektoenablesustainedprofitablegrowth.Belowisasummaryofourcurrentcorporategovernancebodiesandriskmanagementstrategy:

RiskGovernance

Board of Directors.TheCompany’sBoardofDirectors(the“Board”)considerseffectiveidentification,measurement,monitoring,managementandreportingoftherisksfacingourbusinesstobekeyelementsofitsresponsibilitiesandthoseoftheGroupChiefExecutiveOfficerandmanagement.MattersrelatingtoriskmanagementthatarereservedfortheBoardincludeapprovaloftheinternalcontrolsandriskmanagementframeworkandanychangestotheAspenGroup’sriskappetite statement and key risk limits. The Risk Committee of the Board also receives reports at each scheduled meeting covering risk management processesincludingthedesign,operation,useandlimitationsoftheinternalmodel.Theinternalmodelisaneconomiccapitalmodelwhichhasbeendevelopedinternallyforuse in certain business decision-making processes, the assessment of risk-based capital requirements and for various regulatory purposes. As a result of thesearrangements and processes, the Board, assisted by management and the Board Committees, is able to exercise effective oversight of the operation of the riskmanagementstrategydescribedin“—RiskManagementStrategy”below.

Board Committees. The Board delegates oversight of the management of certain key risks to its Risk, Audit, and Conflicts Committees. The Audit andConflicts Committees are comprised entirely of independent directors and the chair of each committee reports regularly to the Board on the committees’discussions.

Risk Committee:ThepurposeoftheRiskCommitteeistoassisttheBoardinitsoversightdutiesinrespectofthemanagementofrisk,including:

• makingrecommendationstotheBoardregardingmanagement’sproposalsfortheriskmanagementframework,riskappetite,keyrisklimitsandtheuseofourinternalmodel;

• monitoringcompliancewiththeagreedAspenGroupriskappetiteandkeyrisklimits;and

• oversightofthestressandscenariotestingprocessestablishedbymanagement.

Audit Committee:TheAuditCommitteeisprimarilyresponsibleforassistingtheBoardinitsoversightoftheintegrityofthefinancialstatements.TheAuditCommitteeisalsoresponsibleforreviewingtheadequacyandeffectivenessoftheCompany’sinternalcontrolsandoversightofbothinternalandexternalauditors.Inaddition,theAuditCommitteeoverseestheCompany’scompliancewithapplicablelawsandregulations.

Conflicts Committee: TheBoardestablishedaConflictsCommitteeinSeptember2020toreviewcertainmaterialtransactionsbetweenAspenHoldingsand/oritssubsidiariesandApollooritsnon-Aspenaffiliatesthatmaypresentaconflictofinterest.

Management Committees: The Aspen Group also has a number of executive management committees which have oversight of certain risk managementprocessesincludingthefollowing:

Group Executive Committee: The Group Executive Committee is the main executive committee responsible for advising the Group Chief ExecutiveOfficeronmattersrelatingtothestrategyandconductoftheAspenGroup’sbusiness.

Investment Committee: The Investment Committee is primarily responsible for setting and monitoring the Aspen Group’s investment risk and assetallocationpoliciesandensuringthattheGroupChiefRiskOfficeriskeptinformedofsuchmatters.

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Risk Management Committee:TheprimarypurposeoftheRiskManagementCommitteeistoassisttheGroupChiefRiskOfficerinheroversightdutiesinrespectofthedesignandoperationoftheAspenGroup’sriskmanagementsystems.Inparticular,theRiskManagementCommitteehasspecificresponsibilitiesin relation to the internal model andfor the establishment of risk limits for accumulating underwriting andinvestment exposures andmonitoringsolvencyandliquidityrequirements.

Reserve Committee: The Reserve Committee is responsible for managing reserving risk and making recommendations to the GroupChief ExecutiveOfficerandtheGroupChiefFinancialOfficerrelatingtotheappropriatelevelofreservestoincludeintheAspenGroup’sfinancialstatements.

Underwriting Committee:ThepurposeoftheUnderwritingCommitteeistoassisttheGroupChiefExecutiveOfficerinhisoversightdutiesinrespectofthemanagementandcontrolofunderwritingrisk,includingoversightoftheindependentreviewofthequalityofeachteam’sunderwriting.

Group Operations Committee:ThepurposeoftheGroupOperationsCommitteeistooverseetheAspenGroup’soperationalsupportfunctionstoensurethattheyarestrategicallyalignedtoprovidecoordinated,efficientandcosteffectiveoperationalsupporttotheexecutionoftheAspenGroup’sunderwritingplans.

RiskManagementStrategy

Weoperateanintegratedenterprise-wideriskmanagementstrategydesignedtoprotectshareholdervalueinasustainableandefficientmannerwhileprovidingahighlevelofpolicyholderprotection.Theexecutionofourintegratedriskmanagementstrategyisbasedon:

• the establishment and maintenance of an internal control and risk management systembased ona three lines of defense approach to the allocation ofresponsibilities betweenrisk accepting units (first line), risk management activity andoversight fromother central control functions (secondline) andindependentassurance(thirdline);

• identifyingmaterialriskstotheachievementoftheAspenGroup’sobjectivesincludingemergingrisks;

• thearticulationatGrouplevelofourriskappetiteandaconsistentsetofkeyrisklimitsforeachmaterialcomponentofrisk;

• thecascadingofriskappetiteandkeyrisklimitsformaterialriskstoeachoperatingsubsidiaryand,whereappropriate,riskacceptingbusinessunits;

• measuring,monitoring,managingandreportingriskpositionsandtrends;

• theuse,subjecttoanunderstandingofitslimitations,oftheinternalmodeltoteststrategicandtacticalbusinessdecisionsandtoassesscompliancewiththeriskappetitestatement;and

• stressandscenariotesting,includingreversestresstesting,designedtohelpusbetterunderstandanddevelopcontingencyplansforthelikelyeffectsofextremeeventsorcombinationsofeventsoncapitaladequacyandliquidity.

Risk Appetite Statement.TheriskappetitestatementisacentralcomponentoftheAspenGroup’soverallriskmanagementframeworkandisapprovedbytheBoard.Itsetsout,atahighlevel,howwethinkaboutriskinthecontextofourbusinessmodel,AspenGroupobjectivesandstrategy,andprovidesthefoundationfor decision making during the implementation of our strategy and business plans. It sets out boundary conditions and limits for the level of risk we assume,togetherwithastatementoftherewardweaimtoreceiveforthislevelofrisk.Ourriskappetitestatementcomprisesthefollowingcomponents:

• Risk preferences:ahighleveldescriptionofthetypesofrisksweprefertoassumeandthoseweprefertominimizeoravoid;

• Return objective:adescriptionofthereturnoncapitalweseektoachieve,subjecttoourriskconstraints;

• Volatility objective:adescriptionofearningsvolatilitytolerance;

• Capital objective:adescriptionofthetargetlevelofriskadjustedcapital;and

• Liquidity objective:adescriptionofthetargetlevelofliquidity.

Risk Components.Themaintypesofrisksthatwefacearesummarizedasfollows:

Insurance risk:Theriskthatunderwritingresultsvaryfromtheirexpectedamounts,includingtheriskthatreservesestablishedinrespectofpriorperiodsdiffersignificantlyfromthelevelofreservesincludedintheAspenGroup’sfinancialstatements.

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Market risk:Theriskofvariationintheincomegeneratedby,andthefairvalueof,ourinvestmentportfolio,cashandcashequivalentsandderivativecontractsincludingtheeffectofchangesinforeigncurrencyexchangerates.

Credit risk: The risk of diminution in the value of insurance receivables as a result of counter-party default. This principally comprises default andconcentrationrisks relatingto amounts receivable fromintermediaries, policyholders andreinsurers. Weincludecredit risksrelatedtoour investment portfolioundermarketrisk.Weincludecreditrisksrelatedtoinsurancecontracts(e.g.creditandpoliticalriskpolicies)underinsurancerisk.

Liquidity risk:Therisksoffailingtomaintainsufficientliquidfinancialresourcestomeetliabilitiesastheyfalldueortoprovidecollateralasrequiredforcommercialorregulatorypurposes.

Operational risk:Theriskoflossresultingfrominadequateorfailedinternalprocesses,personnelorsystems,orfromexternalevents.

Group risk: TheriskthateventsorcircumstancesaffectingoneormorecompaniesintheAspenGroupthreatenthesolvency,liquidityorreputationoftheCompany.

Strategic risk:Theriskofadverseimpactonshareholdervalueorincomeandcapitalofadversebusinessdecisions,poorexecutionorfailuretorespondtomarketchanges.

Regulatory risk:ThepotentialimpactofchangesintheregulatoryandsupervisoryregimesinthejurisdictionsinwhichAspenoperates.Theriskofnon-compliance with regulatory requirements, including ensuring we understand and comply with changes to those requirements is assessed and managed asoperationalrisk.

Taxation risk:Theriskthatwedonotunderstand,planforandmanageourtaxobligationsisassessedandmanagedasoperationalrisk.Thereisaresidualriskthatchangesintaxationimpactourabilitytooperateprofitablyinsomejurisdictionsorsomelinesofbusiness.

Emerging risk:TheriskthateventsorissuesnotpreviouslyidentifiedorfullyunderstoodimpacttheoperationsorfinancialresultsoftheAspenGroup.

Wedistinguishbetween“core”and“non-core”risks.Coreriskscomprisethoseriskswhichareinherentintheoperationofourbusiness,includinginsurancerisks in respect of our underwriting operations and market risks in respect of our investment activity. We actively seek core risks with a view to generatingshareholdervaluebutseektomanagetheresultingvolatilityinourearningsandfinancialconditionwithinthelimitsdefinedbyourriskappetite.However,thesecore risks are intrinsically difficult to measure and manage and we may not, therefore, be successful in this respect. All other risks, including regulatory andoperationalrisks,areclassifiedasnon-core.Weseek,totheextentweregardasreasonablypracticableandeconomicallyviable,toavoidorminimizeourexposuretonon-corerisks.

Risk Limits Frameworks. Aspen’s Risk Limit Framework translates the risk appetite objectives into measurable criteria. Limits provide primary control forGroup-wideaccumulatedriskexposuresandestablishestheconnectionstobusinessplanningbyplacingconstraintsonrisktakingdecisions.

LimitsareestablishedforthemostimportantdriversofriskattheGrouplevelandexpressthemaximumlevelofallowableexposureperriskdriver. Atthehighestlevel,risklimitsareapprovedbytheBoardofDirectors.MonitoringoftheGrouppositionagainsttheselimitsisincludedinregularreportingtotheBoardofDirectorsoritsCommittees.

Business Distribution

Ourbusinessisproducedprincipallythroughbrokersandreinsuranceintermediaries.Thebrokeragedistributionchannelprovidesuswithaccesstoanefficient,global distribution systemwithout the significant time andexpense which would be incurred in creating wholly-owneddistribution networks. The brokers andreinsuranceintermediariestypicallyactintheinterestofinsureds,cedingclientsorinsurersandareinstrumentaltoourcontinuedrelationshipwithourclients.

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ThefollowingtablesshowourgrosswrittenpremiumsbybrokerforeachofourbusinesssegmentsforthetwelvemonthsendedDecember31,2020,2019and2018:

Twelve Months Ended December 31,

2020Twelve Months Ended December 31,

2019Twelve Months Ended December 31,

2018

Reinsurance

GrossWritten

Premiums % of Total

Gross Written

Premiums % of Total

GrossWritten

Premiums % of Total ($ in millions, except for percentages)AonCorporation $ 358.0 21.5 % $ 311.9 21.0 % $ 363.7 24.3 %Marsh&McLennanCompanies,Inc. 358.7 21.6 301.5 20.3 312.1 20.9WillisGroupHoldings,Ltd. 283.4 17.1 278.7 18.8 282.2 18.9Others 660.7 39.8 593.4 39.9 537.7 35.9Total $ 1,660.8 100.0 % $ 1,485.5 100.0 % $ 1,495.7 100.0 %

_______________

OnMarch9,2020,AonplcandWillisTowersWatsonannouncedadefinitiveagreementtocombine,andexpectthetransactiontocloseinthefirsthalfof2021.

Includesgrosswrittenpremiumof$334.8millionrelatedtoCGBDS;(2019—$312.5million(CGBDS);(2018—$259.7million(CGBDS);$33.1million(AgriLogic).

Twelve Months Ended December 31,

2020Twelve Months Ended December 31,

2019Twelve Months Ended December 31,

2018

Insurance

GrossWritten

Premiums % of Total

Gross Written

Premiums % of Total

GrossWritten

Premiums % of Total ($ in millions, except for percentages)AonCorporation $ 226.7 11.1 % $ 147.7 7.5 % $ 180.8 9.3 %Marsh&McLennanCompanies,Inc. 211.5 10.4 165.6 8.5 230.9 11.9RyanSpecialty 151.7 7.4 111.6 5.7 101.1 5.2Brown&BrownInc 122.1 6.0 124.9 6.4 121.9 6.2WillisGroupHoldings,Ltd. 103.1 5.0 76.1 3.9 145.1 7.4CRCSwett 82.2 4.0 76.8 3.9 78.8 4.0CoastalInsuranceUnderwriters,Inc 77.3 3.8 61.0 3.1 56.1 2.9AmWINSGroupInc 74.6 3.7 71.4 3.6 86.4 4.4HealthPlanIntermediariesHoldings 72.0 3.5 14.5 0.7 — —ArthurJGallagher(UK)Limited 62.0 3.0 52.5 2.7 70.8 3.6LocktonInc 59.3 2.9 51.4 2.6 56.0 2.9Others 800.3 39.2 $ 1,003.4 51.4 $ 823.3 42.2Total $ 2,042.8 100.0 % $ 1,956.9 100.0 % $ 1,951.2 100.0 %

______________OnMarch9,2020,AonplcandWillisTowersWatsonannouncedadefinitiveagreementtocombine,andexpectthetransactiontocloseinthefirsthalfof2021.

In early 2020, the U.S. accident and health business expanded their capacity under an existing program arrangement. Soon thereafter in March 2020,followingstrategicreviewswedeterminedtoceaseunderwritingandstartedtowinddownthebusiness.Inanefforttomitigatetherisksassociatedwiththisprogram,insurancemanagemententeredintoa100%quotasharearrangementforthe2020portionoftheprogram.Thepriorperiodsarere-presentedtomirrorthecurrentyearbreakdown.

The2019and2018priorperiodsarere-presentedtoreplicatethecurrentyearbreakdown.

(1)

(2)

(1)

(2)

(3)

(3)

(3)

(3)

(1)

(2)

(1)

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Claims Management

Wehaveastaffofexperiencedclaimsprofessionalsorganizedintoinsuranceandreinsuranceteamswhicharemanagedseparately,butoperateunderaglobalstructuredesignedtoachieveconsistencyandefficienciesacrossalllinesofbusiness.Wehavedevelopedprocessesandinternalbusinesscontrolsforidentifying,trackingandsettlingclaims,andauthoritylevelshavebeenestablishedforallindividualsinvolvedinthereservingandsettlementofclaims.

Thekeyresponsibilitiesofourclaimsmanagementdepartmentsinclude:

• processing, managing and resolving reported insurance or reinsurance claims efficiently and accurately to ensure the proper application of intendedcoverage, reserving in a timely fashion for the probable ultimate cost of both indemnity and expense and making timely payments in the appropriateamountonthoseclaimsforwhichwearelegallyobligatedtopay;

• selectingappropriatecounselandexpertsforclaims,manageclaims-relatedlitigationandregulatorycompliance;

• contributingtotheunderwritingprocessbycollaboratingwithunderwritingteamsandseniormanagementintermsoftheevolutionofpolicylanguageandendorsementsandprovidingclaim-specificfeedbackandeducationregardinglegalactivity;and

• contributingtotheanalysisandreportingoffinancialdataandforecastsbycollaboratingwiththefinanceandactuarialfunctionsrelatingtothedriversofactualclaimreservedevelopmentsandpotentialforfinancialexposuresonknownclaims.

Onthoseaccountswhereitisapplicable,ateamofin-houseclaimsprofessionalsoverseesandregularlyauditsclaimshandledunderoutsourcingagreementsandmanagesthoselargeclaimsandcoverageissuesonreferralasrequiredunderthetermsofthoseagreements.

Seniormanagement receivesaregular report onthestatusof ourreservesandsettlement of claims. Werecognizethat fair interpretationofourreinsuranceagreementsandinsurancepolicieswithourcustomers,andtimelypaymentofvalidclaims,areavaluableservicetoourclientsandenhanceourreputation.

Reserves

UnderU.S.GenerallyAcceptedAccountingPrinciples(“U.S.GAAP”)andapplicableinsurancelawsandregulationsinthecountrieswhereweoperate,wearerequired to establish loss reserves for the estimated unpaid portion of the ultimate liability for losses and loss expenses under the terms of our policies andagreementswithourinsuredandreinsuredcustomers.Theprocessofestimatingthesereservesinvolvesaconsiderabledegreeofjudgmentand,asofanygivendate,isinherentlyuncertain.Forafulldiscussionregardingourlossandlossexpensesreservingprocess,refertoItem5,“OperatingandFinancialReviewandProspects—CriticalAccountingPolicies—ReservingApproach”andItem3D,“RiskFactors—InsuranceRisks—Ourfinancialconditionandoperatingresultsmaybeadverselyaffectedifactualclaimsexceedourlossreserves.”

Investments

Ourinvestmentstrategyisfocusedondeliveringstableinvestmentincomeandtotalreturnthroughallmarketcycleswhilemaintainingappropriateportfolioliquidity and credit quality to meet the requirements of our customers, rating agencies and regulators. To enhance investment returns where possible,wetacticallyadjustthedurationoftheinvestmentportfolioandassetallocationtakingintoaccounttheaverageliabilitydurationofourreinsuranceandinsurancerisksandourviewsofinterestrates,theyieldcurve,creditspreadsandmarketsfordifferentassets.

We maintain an Investment Committee that establishes investment guidelines and supervises our investment activity. The Investment Committee regularlymonitors our overall investment results and performance against our investment objectives and guidelines. These guidelines specify minimum criteria on theoverallcreditqualityandliquiditycharacteristicsoftheportfolio,andincludelimitationsonthesizeofcertainholdingsandrestrictionsonpurchasingcertaintypesofsecurities.ManagementandtheInvestmentCommitteereviewourinvestmentperformanceandassesscreditandmarketriskconcentrationsandexposurestoissuers.Wefollowaninvestmentstrategydesignedtoemphasizethepreservationofcapitalandprovidesufficientliquidityforthepromptpaymentofclaims.

We currently engage Apollo Asset Management Europe PC LLP, BlackRock Financial Management Inc., DWS Investment Management Americas Inc.,Goldman Sachs Asset Management L.P., Conning Asset Management Limited and The Blackstone Group to provide investment advisory and managementservicesforourportfolioofinvestments.Theseagreementsmaybeterminatedgenerallybyeitherpartyonshortnoticewithoutpenalty.

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For additional information concerning our investments, refer to Item 5, “Operating and Financial Review and Prospects”, Item 18, Notes 4 and 6 of ourconsolidatedfinancial statements, “Investments,” and“Fair ValueMeasurements,” respectively. Foradditional informationconcerningCurrent Expected CreditLosses (“CECL”) on Investments, refer to Note 2(c) of our consolidated financial statements, “Basis of Preparation and Significant Accounting Policies —AccountingforInvestments,CashandCashEquivalents.”

Competition

Theinsuranceandreinsuranceindustriesarematureandhighlycompetitive.Competitionvariessignificantlyonthebasisofproductandgeography.Insuranceandreinsurancecompaniescompeteonthebasisofmanyfactors,includingpremiumcharges,generalreputationandperceivedfinancialstrength,thetermsandconditionsoftheproductsoffered,ratingsassignedbyindependentratingagencies,speedofclaimspayments,reputationandexperienceintheparticularrisktobeunderwritten,qualityofservice,thejurisdictionwherethereinsurerorinsurerislicensedorotherwiseauthorized,capacityandcoveragesofferedandvariousotherfactors. Increasedcompetitioncouldresult in fewersubmissionsfor ourproducts andservices, lowerrates charged, slowerpremiumgrowthandless favorablepolicytermsandconditions,anyofwhichcouldadverselyimpactourgrowthandprofitability.

WecompetewithmajorU.S.,U.K.,Bermudian,EuropeanandotherinternationalinsurersandreinsurersandunderwritingsyndicatesfromLloyd’s,someofwhichhavelongeroperatinghistories, morecapital and/ormorefavorablefinancial strengthratingsthanwedo,aswell asgreater marketing, management andbusinessresources.Wealsocompetewithcapitalmarketparticipantsthatcreatealternativeproducts,suchascatastrophebonds,thatareintendedtocompetewithtraditionalreinsuranceproducts.

Ratings

Ratingsbyindependentagenciesareanimportantfactorinestablishingthecompetitivepositionof(re)insurancecompaniesandareimportanttoourabilitytomarket andsell ourproductsandservices. Ratingorganizationscontinuallyreviewthefinancial positionsofinsurers, includingus. Asofthedateoffiling, thefinancialstrengthratingsofourOperatingSubsidiarieswereasfollows:

Rating Agency RatingRated OperatingSubsidiary Agency’s Rating Definition Ranking of Rating

Standard&Poor’sFinancialServicesLLC(“S&P”)

A-(Strong-Stableoutlook)

AspenU.K.andAspenBermuda

Strongcapacitytomeetfinancialcommitmentsbutsomewhatmoresusceptibletotheadverseeffectsofchangesincircumstancesandeconomicconditionsthanthoseinhigher-ratedcategories

The‘A’groupingisthethirdhighestoftenmajorratingcategories.

A.M.Best A(Excellent)(Negative)

AspenU.K.,AspenBermuda,AspenSpecialtyandAAIC

Anexcellentabilitytomeetongoinginsuranceobligations

The‘A’groupingisthesecondhighestofsevenmajorratingcategories.

These ratings reflect the respective opinions of S&P and A.M. Best regarding the ability of the relevant Operating Subsidiary to pay claims and are notevaluationsdirectedtoourinvestorsorrecommendationstobuy,sellorholdoursecurities.Theseratingsaresubjecttoperiodicreviewby,andmaybereviseddownwardorrevokedatthesolediscretionof,S&PandA.M.Best,respectively.

For a discussion of some potential risks relating to the ratings of our Operating Subsidiaries, refer to Item 3D, “Risk Factors — Strategic Risks — OurOperatingSubsidiariesareratedandourLloyd’sbusinessbenefitsfromaratingbyoneormoreofA.M.BestandS&Pandadeclineinanyoftheseratingscouldadverselyaffectourstandingamongbrokersandcustomersandcauseourpremiumsandearningstodecrease”and“RiskFactors—StrategicRisks—Wehaveexperiencedaratingsdowngradeandtherecanbenoassurancethatweandoursubsidiarieswillnotexperienceanyfurtherdowngrades,whichmayresultinanadverseeffectonourbusiness,financialconditionandoperatingresults.”

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Regulatory Matters

General

Thebusinessofinsuranceandreinsuranceisregulatedinmostcountries,althoughthedegreeandtypeofregulationvariessignificantlyfromonejurisdictiontoanother. Compliance obligations are increasingin most jurisdictions as the focus oninsurance regulatory controls has escalated in recent years, with particularemphasisonregulationofsolvency,riskmanagementandinternalcontrols.ThediscussionbelowsummarizesthemateriallawsandregulationsapplicabletoourOperating Subsidiaries and, where relevant, Peregrine andSilverton. Our companies have met or exceeded the solvencymargins andratios applicable to themunderrelevantlawsandregulationsasatDecember31,2020.

Group Supervision

TheBermudaMonetaryAuthority(the“BMA”)actsasthegroupsupervisoroftheAspenGroupandhasnamedAspenBermudaasthedesignatedinsurer.TheBermudaInsuranceAct1978asamended(the“InsuranceAct”)andrelatedgroupsupervisionregulations(collectivelythe“GroupSupervisionRegime”)setoutprovisionsregardinggroupsupervisionandtheresponsibilitiesofthedesignatedinsurer. TheGroupSupervisionRegimeisinadditiontotheregulationoftheCompany’svariousOperatingSubsidiariesintheirlocaljurisdictions.

As the group supervisor, the BMA performs a number of functions including: (i) coordinating the gathering and dissemination of information for otherregulatoryauthorities;(ii)carryingoutsupervisoryreviewsandassessmentsoftheAspenGroup;(iii)carryingoutassessmentsoftheAspenGroup'scompliancewiththerulesonsolvency,riskconcentration,intra-grouptransactionsandgoodgovernanceprocedures;(iv)planningandcoordinating,throughregularmeetingswithotherauthorities,supervisoryactivitiesinrespectoftheAspenGroup;(v)coordinatinganyenforcementactionthatmayneedtobetakenagainsttheAspenGrouporanymemberoftheAspenGroup;and(vi)coordinatingmeetingsofcollegesofsupervisorsinordertofacilitatethecarryingoutofthesefunctions.Asthedesignatedinsurer,AspenBermudaisrequiredtofacilitatecompliancebytheAspenGroupwiththegroupinsurancesolvencyandsupervisionrules.

Annual and Quarterly Filings.Onanannualbasis,theAspenGroupisrequiredtosubmittotheBMA:(i)agroupstatutoryfinancialreturn;(ii)auditedgroupfinancialstatementsincludingnotestothefinancialstatements,inaccordancewithGAAPStandards(“GroupFinancialStatements”);and(iii)agroupcapitalandsolvencyreturn,whichincludestheGroupBermudaSolvencyCapitalRequirement(“BSCR”),arisk-basedcapitaladequacymodel,andassociatedschedules,aGroup Solvency Self-Assessment (“GSSA”), a Financial Condition Report (the “FCR”) and an opinion of a BMAapproved Group Actuary on the economicbalancesheettechnicalprovisions.Inaddition,theAspenGroupfilesquarterlygroupfinancialreturnswiththeBMA.TheGSSAisaself-assessmentofourriskand solvency requirements that allows the BMA to obtain our view of the capital resources required to achieve our business objectives and to assess ourgovernance, riskmanagement andcontrols surroundingthis process. TheGroupFinancial Statements arepublishedbytheBMAonits websiteandtheFCRispublishedonourwebsite.

Group Minimum Solvency Margin and Group Enhanced Capital Requirements. Aspen Holdings must ensure that the group’s statutory assets exceed theamount of its statutory liabilities bythe aggregate minimummargin of solvencyof each qualifying member of the insurance group. Amember is a qualifyingmemberifitissubjecttosolvencyrequirementsinthejurisdictioninwhichitisregistered.

Inaddition,everyinsurancegroupmustmaintainavailablestatutorycapitalandsurplusinanamountequaltoorexceedingitsEnhancedCapitalRequirement(“ECR).TheECRisdeterminedeitherbyreferencetotheBSCRmodeloranapprovedinternalcapital model.TheAspenGroupcurrentlyreliesontheBSCRmodeltoestablishitsECR.TheBMAalsoexpectsinsurancegroupstooperateatoraboveagroupTargetCapitalLevel(“TCL”),whichtheBMAhassetat120%ofthegroupECR.TheAspenGroupholdscapitalinexcessofitsTCLasatDecember31,2020.

Bermuda

AspenBermudaislicensedasaClass4insurerandissubjecttotheInsuranceAct, whichimposessolvencyandliquiditystandardsaswell asauditingandreportingrequirementsonBermudainsurersandreinsurers,anditempowerstheBMAtosupervise,investigate,requireinformationandinterveneintheaffairsofBermudaregisteredinsurancecompanies.ThereareanumberofremedialactionstheBMAcantaketoprotectthepublicinterestifitdeterminesthataBermudainsurerorreinsurermaybecomeinsolventorthatabreachoftheInsuranceActorofaregistrationconditionhasoccurredorisabouttooccur.

InadditiontorequiringtheappointmentofaprincipalrepresentativeinBermuda,theappointmentofanindependentauditor,theappointmentofalossreservespecialistandthefilingofvariousfinancialstatementsandreturns,significantprovisionsoftheInsuranceActapplicabletoAspenBermudainclude:

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Enhanced Capital Requirements.SimilartotheGrouprequirements,inordertominimizetheriskofashortfallincapitalarisingfromanunexpectedadversedeviation,theBMAexpectsClass4insurerssuchasAspenBermudatomaintainaTCLequalto120%ofitsECR.AsatDecember31,2020,AspenBermudaholdscapitalinexcessofitsTCL.

Minimum Solvency Margin and Minimum Liquidity Ratio.AspenBermudaisalsorequiredtocomplywithaminimumsolvencymarginandminimumliquidityratio in respect of its business. The minimum solvency margin is the greater of: (i) $100,000,000; or (ii) 50% of net written premiums (being gross writtenpremiumslessanypremiumsceded(notexceeding25%ofgrosspremiums))initscurrentfinancialyear;or(iii)15%ofnetlossesandlossexpenseprovisionsandotherinsurancereserves;or(iv)25%oftheECRreportedattheendofitsrelevantyear.Theminimumliquidityratiorequiresthatthevalueofrelevantassetsnotbelessthan75%oftheamountofrelevantliabilities.

Restrictions on Dividends, Distributions and Reduction of Capital.AspenBermudamaynotdeclareorpayanydividendsduringanyfinancialyearifitwouldcausetheinsurertofailtomeetitsrelevantsolvencymargins,capitalrequirementsorliquidityratio,andaninsurerwhichfailstomeetitsrelevantrequirementsonthelastdayofanyfinancialyearmaynot,withouttheapprovaloftheBMA,declareorpayanydividendsduringthenextfinancialyear.Inaddition,asaClass4insurer,AspenBermudamaynotinanyfinancialyearpaydividendswhichwouldexceed25%ofitstotalstatutorycapitalandsurplus,asshownonitsstatutorybalancesheetinrelationtothepreviousfinancialyear,unlessitfileswiththeBMAasolvencyaffidavitatleastsevendaysinadvance.Further,AspenBermudamustobtainthepriorapprovaloftheBMAbeforereducingby15%ormoreitstotalstatutorycapitalassetoutinitspreviousyear’sfinancialstatements.

TheInsuranceAmendment(No.2)Act2018amendedtheBermudaInsuranceAct1978toprovideforthepriorpaymentofpolicyholders’liabilitiesaheadofgeneral unsecured creditors in the event of the liquidation or winding up of an insurer. The amendments provide among other matters that, subject to certainstatutorilypreferreddebts,theinsurancedebtsofaninsurermustbepaidinprioritytoallotherunsecureddebtsoftheinsurer.Insurancedebtisdefinedasadebttowhichaninsurerisormaybecomeliablepursuanttoaninsurancecontractexcludingdebtsowedtoaninsurerunderaninsurancecontractwheretheinsureristhepersoninsured.

Inaddition,ourBermudacompanies,includingAspenHoldingsandAspenBermuda,mustcomplywiththeprovisionsoftheBermudaCompaniesAct1981,asamended (the “Companies Act”), regulating the payment of dividends and distributions. A Bermuda company may not declare or pay a dividend or make adistribution out of contributed surplus if there are reasonable grounds for believing that: (i) the company is, or would after the payment be, unable to pay itsliabilitiesastheybecomedue;or(ii)therealizablevalueofthecompany’sassetswouldtherebybelessthanitsliabilities.

Peregrine and Silverton

Special Purpose Insurers and Segregated Account Companies.PeregrineandSilvertonareregisteredasSPIsundertheBermudaInsuranceAct1978licensedto carry onspecial purpose business. Special purpose business is defined under the Insurance Act as insurance business under whichan insurer fully funds itsliabilitiestothepersonsinsured.

Unlikeother(re)insurers,SPIsarefullyfundedtomeettheir(re)insuranceobligationsandaredeemed“bankruptcyremote”.Asaresult,theapplicationandsupervisionprocesses are streamlined to facilitate the transparent structure. SPIs are required to file electronic statutory financial returns andthe BMAhasthediscretiontomodifysuchinsurer’sstatutoryfilingsrequirementsundertheBermudaInsuranceAct1978.Likeother(re)insurers,theprincipalrepresentativeofanSPIhasadutytoinformtheBMAinrelationtosolvencymatters,whereapplicable.

Segregated Account Companies. Peregrine and Silverton are also registered as segregated accounts companies under the Bermuda Segregated AccountsCompaniesAct2000,asamended.Asasegregatedaccountscompany,PeregrineandSilvertonarerequiredtosegregatetheassetsandliabilitieslinkedtotheirrespective segregated accounts from the assets and liabilities linked to their other respective segregated accounts and from their general account assets andliabilities. The segregated account representative of a segregated accounts company has the duty to informthe Registrar of Companies in relation to solvencymattersandnon-compliance,whereapplicable.

Economic Substance

Parent,theCompanyandcertainofourBermuda-domiciledsubsidiariesarealsosubjecttotheEconomicSubstanceAct2018,asamended,andtheEconomicSubstance Regulations 2018, as amended (together the “ESA”). The ESA was enacted to demonstrate Bermuda’s commitment to comply with internationalstandardswithrespecttocooperationfortaxpurposesandtoensurethatBermudadoesnotfacilitatetheuseofstructureswhichattractprofits,butwhichdonotreflect real economic activity within Bermuda. The ESA provides that a registered entity other than an entity which is resident for tax purposes in certainjurisdictionsoutsideBermuda(“non-residententity”)thatcarriesonasabusinessanyoneormoreofthe“relevantactivities”referredtointheESAmustcomplywitheconomicsubstancerequirements.Thelistof“relevantactivities”includescarryingonanyoneormoreofthefollowingactivities:banking,insurance,fundmanagement,financing,leasing,headquarters,

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shipping,distributionandservicecenter,intellectualpropertyandholdingentities.UndertheESA,ifacompanyisengagedinoneormore“relevantactivities”,itisrequiredtomaintainasubstantialeconomicpresenceinBermudaandtocomplywiththeeconomicsubstancerequirementssetforthintheESA.Acompanywillcomplywiththoseeconomicsubstancerequirementsifit:(a)ismanagedanddirectedinBermuda;(b)undertakes“coreincomegeneratingactivities”(asmaybeprescribed under the ESA) in Bermuda in respect of the relevant activity; (c) maintains adequate physical presence in Bermuda; (d) has adequate full timeemployeesinBermudawithsuitablequalifications;and(e)incursadequateoperatingexpenditureinBermudainrelationtotherelevantactivityundertakenbyit.

TheESArequiresentitiessubjecttoittomakeannualfilingswiththeBermudaRegistrarofCompaniestodemonstratetheeconomicsubstanceoftheentity’sactivitiesandbusinessinBermuda.CompaniesthatarelicensedtoandcarryoninsuranceasarelevantactivityaregenerallyconsideredtooperateinBermudawith adequate substance, with respect to their insurance business, if they comply with the existing provisions of (a) the Companies Act elating to corporategovernance; and (b) the Insurance Act, that are applicable to the economic substance requirements, and the Registrar will have regard to such companies’compliance with the Insurance Act (in addition to compliance with the Companies Act) in his assessment of compliance with the economic substancerequirements.ForthoseAspenentitiessubjecttotheESA,weexpectthatthefilingswillcontinuetomeettheESArequirements.

Privacy Laws

TheBermudaPersonalInformationProtectionAct2016(PIPA)regulateshowanyindividual,entityorpublicauthoritymayusepersonalinformation.PIPAreflectsasetofinternationallyacceptedprivacyprinciplesandgoodbusinesspracticesfortheuseofpersonalinformation.AlthoughPIPAwaspassedonJuly27,2016,thesectionsthatarecurrentlyineffectarelimitedtothosethatrelatetotheestablishmentandappointmentofthePIPAcommissioner(PIPACommissioner),the hiring of the PIPA Commissioner’s staff, and the general authority of the PIPA Commissioner to inform the public about PIPA. Following the PIPACommissioner’s appointment, effective January 20, 2020. On October 30, 2020 the PIPA Commissioner issued guidance regarding privacy safeguarding ofpersonalinformationbypubliccompanies,however,PIPA’sremainingprovisionshavenotbeenfullyimplementedandregulationsunderPIPAhavenotyetbeenprovided.

Inaddition,theInsuranceAmendmentActof2020becameoperativeinAugust2020andrequiresentitiesregulatedbytheBMAtoprovidenoticetotheBMAof certain cybersecurity events. As a result, the BMA’s Insurance Sector Operational Cyber Risk Management Code of Conduct, which includes a series ofminimumandrecommendedcybersecuritystandards,becameeffectiveonJanuary1,2021.

U.K. and E.U. Regulation

General. Aspen U.K. is authorized by the PRA to effect and carry out (re)insurance contracts in the U.K. in classes of general (non-life) business and isregulatedbyboththePRAwithrespecttoprudentialmattersandbytheFCAwithrespecttotheconductofitsbusiness.AMALisauthorizedbythePRAandregulatedbythePRAwithrespecttoprudentialmattersandtheFCAwithrespecttotheconductofitsbusiness.AUKSSLisauthorizedandregulatedbytheFCAwithrespecttoprudentialandconductofbusiness.

Prior to the United Kingdom’s decision to withdraw from the E.U. customs union and single market, an insurance company with authorization to writeinsurancebusinessintheU.K.couldprovidecross-borderservicesinothermemberstatesoftheEEAsubjecttohavingnotifiedtheappropriateEEAhoststateregulatorviathePRApriortocommencementoftheprovisionofservicesandtheappropriateEEAhoststateregulatornothavinggoodreasontorefuseconsent.AspenU.K.hadnotifiedtheFinancial ServicesAuthority(thePRA/FCA’spredecessor) ofits intentiontowriteinsuranceandreinsurancebusinessinall otherEEAmemberstates. Asaresult, priortoBrexit, AspenU.K.waslicensedtowriteinsurancebusinessunderthe“freedomofservices”withinall EEAmemberstates(freedomofservicesandfreedomofestablishmentrightstogether, “PassportingRights”)containedintheEuropeanCouncil’sInsuranceDirectives. AlsopriortoBrexit,asageneralinsurer,AspenU.K.wasalsoabletocarryoutreinsurancebusinessonacross-borderservicesbasisacrosstheEEA.

Brexit Update

AsaresultofBrexitconcludingonDecember31,2020,AspenU.K.lostitsEEAfinancialservicesPassportingRights.However,AMALcontinuestobeabletoaccesstheEEAmarketthroughLloyd’sInsuranceCompany,S.A.inBrussels(“Lloyd’sBrussels”).Lloyd’sBrusselscommencedunderwritingallnon-liferisksfromnon-U.K.EEAcountriesfromJanuary1,2019.OurbusinesswrittenthroughLloyd’sBrusselsstamp5383is100%reinsuredbySyndicate4711.

Inaddition,AspenBermudaestablishedabranchinZurich,Switzerlandin2019towritepropertyandcasualtyreinsurancewithinceptiondatesofJanuary1,2020andlater.

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In2020,AspenU.K.contactedallthirtyEEAregulatorswhereAspenU.K.hadwrittenpoliciestoadvisethemthatAspenU.K.hadceasedwritinginsurancebusiness in their jurisdiction, and that Aspen U.K. would not actively underwrite new insurance risks, renew risks, or make mid-term adjustments to existingpolicies in their jurisdiction. Aspen U.K. requested their permission to continue to collect premiums and pay claims (including those that arise in the future)withoutrequiringlocalauthorization.

Confirmation has been received from twenty-four EEA regulators that Aspen U.K. is permitted to continue collecting premium and paying claims undertemporary transitional arrangements. Four EEA regulators have not agreed to Aspen U.K.’s request, of which only Sweden has live policies and claimsoutstanding. The only actions that Aspen U.K. can take in Sweden is the cancellation of policies and return of premiums. Neither of the remaining two EEAregulators whofailedto respondtoAspenU.K.havelive policies or claims. AspenU.K.is nowwritingto certain EEAregulators whohaverequestedfurtherinformation(e.g.run-offplans)tocomplywiththeirtemporarytransitionalarrangements.

FormoreinformationontheuncertaintysurroundingtheimplementationandeffectofBrexit,refertoItem3D,“RiskFactors-RegulatoryRisks-TheUnitedKingdom’swithdrawalfromtheE.U.couldadverselyimpactourbusiness,resultsofoperationsandfinancialcondition”.

SolvencyRequirements.AspenU.K.,AspenEuropeanHoldingsLimited(“AspenEuropean”)andAMAL(byvirtueofbeingamanagingagentofLloyd’s)arerequiredtomeeteconomicrisk-basedsolvencyrequirementsundertheE.U.directivecoveringthecapitaladequacy,riskmanagementandregulatoryreportingforinsurers (the “Solvency II Directive”). The Solvency II Directive, together with European Commission “delegated acts’ and guidance issued by the EuropeanInsuranceandOccupationalPensionsAuthority(“EIOPA”)setoutclassificationandeligibilityrequirements,includingthefeatureswhichcapitalmustdisplayinordertoqualifyasregulatorycapital.

Despite the Brexit transitional periodcomingto anend, the EuropeanUnion(Withdrawal) Act 2018, as amended, has transposedall applicable direct E.U.legislation into domestic U.K. law, thus ensuringthe continuing application of the regulatory framework brought about bythe SolvencyII Directive under theU.K.’sfinancialservicesregulatoryregime.

Currently,theEuropeanCommissionisundertakingareviewoftheSolvencyIIDirective,togetherwiththeassociatedEuropeanregulationsandtheEuropeanCommissiondelegatedacts(“SolvencyII”)andguidancetoensurethattheregimeremainsfitforpurpose,callinguponEIOPAtoprovidetechnicaladvicewithEIOPApublishingitsOpiniononDecember17,2020.TheCommission’sproposalonthereviewisexpectedforQ32021.

InJune2020,theU.K.governmentrevealedplanstoreviewSolvencyIItoensurethatitisproperlytailoredtotakeaccountofthestructuralfeaturesoftheU.K. insurance sector, with Her Majesty’s Treasury publishing a ‘Call for Evidence’ in October 2020, outlining the motives behind the review and invitingfeedback on various areas, including, amongst others, the standard formula for capital requirements, the risk margin, the matching adjustment and reportingrequirements.Theresultsofthereviewarenotexpectedtobepublisheduntillaterin2021.

TheSolvencyIIDirectiverequiresinsurerstomaintainminimumSolvencyCapitalRequirement(“SCR”),whichiscalculatedbyanapprovedinternalcapitalmodelorbyastandardformulaprescribedbyEIOPAinaccordancewiththeSolvencyIIDirective.AspenU.K.andAspenEuropeanhavereceivedapprovalfromthePRA,andAMALhasreceivedapprovalfromLloyd’s,touseanagreedInternalModeltocalculatetheirrespectiveSCR.AspenU.K.andAMALarerequiredto ensure that the Internal Model operates properly on a continuous basis and that it continues to comply with the “Solvency Capital Requirements - InternalModels”provisionsassetoutinthePRArulebookandSolvencyII,and,withrespecttoAMAL,withintheLloyd’sminimumstandards.IfAspenU.K.failstocomplywiththeserequirements,thePRAmayrevokeitsapprovalforAspenU.K.tousetheInternalModel.Inaddition,failuretoadequatelycaptureareasofrisk(includingasmaybeidentifiedintheOwnRiskandSolvencyAssessment(“ORSA”)inthecalculationoftheSCRmayresultinthePRAapplyingacapitaladd-on to the SCRcalculated by the Internal Model. Aspen U.K. must also maintain the ability to calculate its SCRusing the Standard Formula as prescribed byEIOPA.

AspenU.K.andAMALarerequiredtomaintainaminimummarginofsolvencyequivalenttotheirSCRatalltimes,thecalculationofwhichdependsonthetypeandamountofinsurancebusinesswrittenaswellasreserve,credit,marketandoperationalrisks.ThefinancialresourcesmaintainedinsupportoftheSCRmustbeadequate,bothastoamountandquality,toensurethatthereisnosignificantriskthatanentity’sliabilitiescannotbemetastheyfalldue.IfthePRAwithrespecttoAspenU.K.orLloyd’swithrespecttoAMAL,considersthatthereareinsufficientcapitalresources,itcanimposeadditionalrequirementsinrelationtotheamountandqualityoftheresourcesitconsidersnecessary.Anyfailuretocomplywithsuchrequirementsintroducedbyregulatorscanresultininterventionbyregulatorsorimpositionofsanctions,whichcouldhaveanadverseeffectonAspenU.K.and/orAMAL’sresultsandfinancialposition.

Solvency II Regime Reports and Returns.UndertheSolvencyIIDirectiveregime,AspenU.K.isrequiredtosubmitquarterlyandannualfilingswiththePRA,includinganannualSolvencyandFinancialConditionReport(“SFCR”),which

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mustalsobepostedonAspen’swebsite.AspenU.K.mustsubmitanannualORSAtothePRA.TheORSAreportisproducedannuallyandprovidesasummaryofalloftheactivityandprocessesduringtheprecedingyeartoassessandreportonrisksandensurethatouroverallsolvencyneedsaremetatalltimesincludingaforward-lookingassessment.It alsoexplainsthelinkagesbetweenbusinessstrategy,businessplanningandcapitalandriskmanagementprocesses.In2016,thePRAgrantedAspenU.K.awaiverforfiveyearsabsolvingitfromtherequirementtoproducecertainregulatoryreturnsattheEEA-sub-grouplevelduetoAspenBermudabeingsubjecttoequivalentgroupsupervision.

Restrictions on Dividend Payments. The companylawof Englandand Wales prohibits English companies, including AspenU.K., AMALandAUL, fromdeclaring dividends to their shareholders unless they have profits available for distribution. The determination of whether a company has profits available fordistributionisbasedonitsaccumulatedrealizedprofitsandotherdistributablereserveslessitsaccumulatedrealizedlosses.WhiletheU.K.insuranceregulatoryrulesimposenostatutoryrestrictionsonageneral insurer’sabilitytodeclareadividend,thePRA’srulesrequireeachauthorizedinsurancecompanywithinitsjurisdiction to maintain its solvency margin at all times. Accordingly, AspenU.K., AMALandAULmaynot paya dividend if the payment of such dividendwouldresultintheirSCRcoverageratiofallingbelowcertainlevels.Inaddition,anyfuturechangesregardingregulatoryrequirements,includingthosedescribedabove,mayrestricttheabilityofAspenU.K.,AMALandAULtopaydividendsinthefuture.

Brexit and the U.K. GDPR.FollowingtheendoftheBrexitTransitionPeriodonDecember,312020,theE.U.GDPRhasbeenimplementedintheU.K.(the“U.K.GDPR”).UndertheU.K.GDPR,companiesnotestablishedintheU.K.butwhoprocesspersonaldatainrelationtotheofferingofgoodsorservicestoindividualsintheU.K.,ortomonitortheirbehaviorwillbesubjecttotheU.K.GDPRandwillberequiredtoappointadataprotectionrepresentativeintheU.K.,providedcertainexceptionsarenotmet.Otherwise,therequirementsoftheU.K.GDPRarevirtuallyidenticaltothoseoftheE.U.GDPRandassuch,mayleadtosimilarcomplianceandoperationalcosts.ForinformationonE.U.GDPR,refertoItem3,“RiskFactors—OtherOperationalRisks—Evolvingprivacyanddatasecurityregulationscoulddamageourreputationandcauselosses.”

Inaddition,BrexithasimplicationsfortransfersofpersonaldatabetweentheU.K.andtheE.U.andviceversa.TransfersofpersonaldatafromtheU.K.totheE.U.areunrestrictedanddonotrequireadditionalsafeguardsastheU.K.hasformallyapprovedtheadequacyoftheE.U.andall12nationsdeemedadequatebytheE.U.AsregardstransfersofpersonaldatafromtheEEAtotheU.K,underthetermsoftheTradeandCooperationAgreementagreedbetweentheE.U.andU.K.onDecember24,2020,suchdataflowsremainunrestricteduntiltheendofJune2021,providedtheU.K.makesnosubstantivechangestoitsdataprotectionlaws. During this “bridging period”, the European Commission will assess the adequacy of the U.K. from a data protection law perspective. If the EuropeanCommissionweretogranttheU.K.an“adequacydecision”,transfersofpersonaldatafromtheEEAtotheU.K.wouldcontinueunrestrictedandwouldnotrequireanyadditionalsafeguards.TotheextenttheEuropeanCommissiondoesnotgranttheU.K.anadequacydecisionasattheendofthebridgingperiod,datatransfermechanismswillneedtobeputinplacetolegitimizethetransferofpersonaldatafromtheEEAtotheU.K.

Branch Regulations

General

AspenU.K.andAspenBermudaarerequiredtomeetlocalcapitalrequirementsandmakerequiredlocalregulatoryfilingsinconnectionwiththeirrespectivebranchofficeoperations.

Switzerland

In2019,ABLestablishedabranchinZurich,Switzerlandtowritepropertyandcasualtyreinsurance.AbranchthatwritesonlyreinsuranceisnotsubjecttosupervisionundertheInsuranceSupervisionAct(Switzerland)bytheFinancialMarketsSupervisoryAuthority(“FINMA”).

AspenU.K.establishedapropertyandcasualtyreinsurancebranchinZurich, Switzerlandin2007.In2010,AspenU.K.establishedaninsurancebranchinZurich,Switzerland,whichwasregulatedbyFINMApursuanttotheInsuranceSupervisionAct(Switzerland).In2017,AspenU.K.discontinuedwritinginsurancebusinessviatheinsurancebranchinSwitzerland. In2020,AspenU.K.ceasedwritingreinsuranceviathereinsurancebranchinSwitzerland,however, FINMAmaintainssupervisionovertheAspenU.K.branchwhilethebusinessisinrunoff.

Singapore

InFebruary2021,ABLreceivedapprovalfromtheMonetaryAuthorityofSingapore(“MAS”)toestablishareinsurancebranchinSingapore.TheactivitiesofthisbranchareregulatedbytheMASpursuanttoTheInsuranceActofSingapore.ABLisalsoregulatedbytheAccountingandCorporateRegulatoryAuthority(“ACRA”)asaforeigncompanyinSingapore.

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AspenU.K.hasalsoestablishedareinsurancebranchinSingaporethatisregulatedbytheMASandpursuanttoTheInsuranceActofSingaporeandbyACRAasaforeigncompanyinSingapore.WeintendtotransitionthebusinesscurrentlywrittenthroughourAspenU.K.branchinSingaporetothenewlyestablishedABLbranchbeginninginthesecondquarterof2021.

AMALsetupasubsidiarycompany,AspenSingaporePte.Ltd.(“ASPL”),toaccessinsurancebusinessinSingaporeandregulatoryapprovalforASPLtoactasanintermediarywasreceivedfromMASin2015.ASPLwasincorporatedbyACRAin2015asalocalcompanyregulatedbytheCompaniesActofSingapore.

Canada

AspenU.K.establishedaCanadianbranchin2006whoseactivitiesareregulatedbytheOfficeoftheSuperintendentofFinancialInstitutions(“OSFI”).OSFIisthefederalregulatoryauthoritythatsupervisesCanadianandnon-CanadianinsurancecompaniesoperatinginCanadapursuanttotheInsuranceCompaniesAct(Canada).Inaddition,thebranchissubjecttothelawsandregulationsofeachoftheprovincesandterritoriesinwhichitislicensed.

Australia

In2008,AspenU.K.receivedauthorizationfromtheAustralianPrudentialRegulationAuthority(“APRA”)toestablishabranchinAustralia.Theactivitiesofthe Australian branch are regulated by APRApursuant to the Insurance Act of Australia 1973. Aspen U.K. is also registered by the Australian Securities andInvestmentsCommissionasaforeigncompanyinAustraliaundertheCorporationsActofAustralia2001.

Foradditionalinformationonourbranches,refertoItem18,Note20(a)ofourconsolidatedfinancialstatements,“CommitmentsandContingentLiabilities-RestrictedAssets.”

Other Regulated Firms

AUKSSL(previouslyAPJServicesLimited)isauthorizedandregulatedbytheFCAandissubjecttoaseparateprudentialregimeandotherrequirementsforinsuranceintermediariesundertheFCAHandbook.

Until February 7, 2020, ARMLwasalso authorized andregulated bythe FCA.ARMLceased bindingbusiness in July 2019and, because AspenU.K. hasassumedARML’sunderwritingadministrationandclaimshandlingobligationsfortherunoffbusiness,ARMLwasvoluntarilyde-authorized.

Dubai

AUKSSL established a branch in Dubai through which it places reinsurance business into Aspen U.K. The Dubai Financial Services Authority DFSAconfirmeditsapprovalofthebranchin2015.InNovember2019,wedeterminedtoclosetheDubaibranch.TheDubaiBranchwasvoluntarilydeauthorizedinApril2020andthebranchclosureprocessisexpectedtobecompletedinthefirsthalfof2021.

Lloyd’s Regulation

General. TheoperationsofSyndicate4711aresubjecttoregulationandsupervisionofthePRA,FCAandtheCouncilofLloyd’s.AMAListhemanagingagent for Syndicate 4711 and AUL provides underwriting capacity to Syndicate 4711 and is a Lloyd’s corporate member. The FCA and PRA both regulateinsurers, insurance intermediaries and Lloyd’s itself. Lloyd’s establishes Minimum Standards for all managing agents to maintain that are designed to meetapplicableregulatoryrequirements.

Solvency Requirements. UnderwritingcapacityofamemberofLloyd’smustbesupportedbyprovidingadeposit(referredtoas“FundsatLloyd’s”)intheformofcash, securities or letters of credit in anamountdeterminedinaccordancewithLloyd’s requirements andtheSolvencyII regime. Theamountof suchdepositiscalculatedforeachmemberthroughthecompletionofanannualcapitaladequacyexercise. Undertheserequirements, Lloyd’smustdemonstratethateachmemberhassufficientassetstomeetitsunderwritingliabilitiesplusarequiredsolvencymargin.

Intervention Powers. TheCouncilofLloyd’shaswidediscretionarypowerstoregulatemembers’underwritingatLloyd’s.It may,forinstance,changethebasisonwhichsyndicateexpensesareallocatedorvarytheFundsatLloyd’sortheinvestmentcriteriaapplicabletotheprovisionofFundsatLloyd’s.Exercisingany of these powers might affect the return on an investment of the corporate member in a given underwriting year. Further, the annual business plans of asyndicatearesubjecttothe

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review and approval of the Lloyd’s Franchise Board. The Franchise Board is responsible for setting risk management and profitability targets for the Lloyd’smarketandoperatesabusinessplanningandmonitoringprocessforallsyndicates.

EachmemberofLloyd’sisrequiredtocontributeapercentageofthatmember’sunderwritingcapacityfortherelevantyearofaccounttotheLloyd’scentralfund(the“Central Fund”). If a memberof Lloyd’sis unabletopayits debts topolicyholders, suchdebts maybepayablebytheCentral Fund,whichinmanyrespects actsasanequivalent toastateguarantyfundintheU.S.If Lloyd’sdeterminesthat theCentral Fundneedstobeincreased, it hasthepowertoassesspremiumleviesoncurrentLloyd’smembers.TheCouncilofLloyd’shasdiscretiontocallorassessuptoanadditional3%ofamember’sunderwritingcapacityinanyoneyearasaCentralFundcontribution.Oursyndicatecapacityforthe2020underwritingyearis$565.0million(2019underwritingyear-$717.6million).

Lloyd’s Brussels. Lloyd’sBrusselsisauthorizedandregulatedbytheNationalBankofBelgium(“NBB”)andregulatedbytheFinancialServicesandMarketsAuthority (Belgium) (“FSMA”). Lloyd’s Brussels is an authorized insurance company licensed to write non-life risks across the EEA and the U.K. and alsomaintains 19branches across Europe. AMALacts as an outsource provider for Lloyd’s Brussels and, as such, AMALis required to comply with policies andoperatingguidelinesmandatedbyLloyd’sBrusselsinordertomeetNBB,FSMAandotherEuropeanregulatoryrequirementsapplicabletoLloyd’sBrussels.

Jersey Regulation

In 2010, wepurchased APJJersey, a Jersey registered insurance companywhichis subject to the jurisdiction of the Jersey Financial Services Commission(“JFSC”).TheJFSCsetsthesolvencyregimeforinsurancecompaniesunderitsjurisdiction.APJJerseyholdsfundsinexcessoftheminimumrequirement.APJJerseyceasedunderwritingnewbusinessinApril2020andwasplacedintorun-offinJune2020.

U.S. Regulation

General. Our U.S. operations are subject to extensive governmental regulation and supervision by the states and jurisdictions in which insurance entitiesoperatingintheU.S.aredomiciled,licensedand/oreligibletoconductbusiness.AAICislicensedtowriteinsuranceonanadmittedbasisinall50U.S.states,theDistrictofColumbia,PuertoRico,GuamandtheU.S.VirginIslands.AspenSpecialtyislicensedinNorthDakotaandiseligibletowritesurpluslinespoliciesinall50U.S.statesandtheDistrictofColumbia.AspenU.K.andSyndicate4711arenotlicensedtowriteinsuranceonanadmittedbasisinanystateintheU.S.,butarealieninsurers eligible towrite surpluslinesbusinessinall 50U.S.states, theDistrict of Columbiaandother U.S.jurisdictionsbasedontheir listingintheQuarterly Listing of Alien Insurers of the International Insurers Department (“IID”) of the National Association of Insurance Commissioners (“NAIC”), theorganization that works to promote standardization of best practices and assists state insurance regulatory authorities and insurers in the U.S.bypromulgatingmodelinsurancelawsandregulationsforadoptionbythestates.However,modelinsurancelawsandregulationsareonlyeffectivewhenadoptedbythestates.Pursuant to IID requirements, Aspen U.K. and Syndicate 4711 have established a U.S. surplus lines trust fund to secure obligations under U.S. surplus linespolicies.AsofDecember31,2020,AspenU.K.’sandSyndicate4711’ssurpluslinestrustfundwas$208.0million.

TheinsurancelawsandregulationsofourU.S.subsidiaries’domiciliarystateshavethemostsignificantimpactonourU.S.operationsaswellastheleadstateregulatorofaninsuranceholdingcompanysystem.AAICisdomiciledinTexasandAspenSpecialtyisdomiciledinNorthDakota.FollowingtheMerger,AAICandAspenSpecialty becamepart of the Apollo Global Management Groupholdingcompanysystem. Theleadstate insurance regulator for the Apollo GlobalManagementGroupholdingcompanysystemistheIowaInsuranceDivision.

Generally, U.S.statesregulateinsuranceholdingcompaniestoassurethefairnessof inter-affiliate transactions, theproprietyof dividendspaidtocorporateparentsandthebenefitsofanyproposedchangeofcontroltransaction.Statesalsoregulateinsurersolvency,accountingmattersandriskmanagement,aswellasarangeofoperational matters, includingauthorizedlinesof business, permittedinvestments, policyformsandpremiumrates for admittedcompanies, maximumsingle policy risks, adequacy of reserves for losses and unearned premiums and maintenance of in-state deposits for the benefit of policyholders. To monitorcompliance, state insurancedepartments performperiodic market conduct examinations andfinancial fitness examinations, andrequire thefilingof annual andotherreportsrelatingtothefinancialconditionofcompaniesandothermatters.CertainU.S.regulatoryrequirementsarehighlightedbelow.

Although the U.S. federal government does not directly regulate the insurance business, federal legislation and administrative policies in several areas cansignificantly affect the insurance business. The Dodd-Frank Wall Street Reformand Consumer Protection Act (the “Dodd-Frank Act”) established the FederalInsuranceOffice(the“FIO”)withintheU.S.DepartmentoftheTreasuryheadedbyaDirectorappointedbytheTreasurySecretary.Whilecurrentlynothavingageneralsupervisoryorregulatoryauthorityoverthebusinessofinsurance,theDirectoroftheFIOperformsvariousfunctionswith

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respect to insurance. The Director of the FIO has also submitted reports to the U.S. Congress on (i) modernization of U.S. insurance regulation (provided inDecember2013)and(ii)theU.S.andglobalreinsurancemarket(providedinNovember2013andJanuary2015,respectively).SuchreportscouldultimatelyleadtochangesintheregulationofinsurersandreinsurersintheU.S.Inaddition,AAICisacertifiedsuretycompanyapprovedbytheU.S.DepartmentoftheTreasuryandissubjecttofederalregulationsrelatedtoTreasurycertifiedsureties.

State Insurance Holding Company Acts.All U.S. states havelawsregulatinginsuranceholdingcompanysystems. Theselawsrequire insurancecompanies,whichareformedandcharteredinthestate(referredtoas“domesticinsurers”),toregisterwiththestatedepartmentofinsurance(referredtoastheir“domesticstate or regulator”) and file information concerning the operations of companies within the holding company systemthat may materially affect the operations,managementorfinancialconditionoftheinsurerswithinthesystem.Insuranceholdingcompanyregulationsprincipallyrelateto(i)stateinsuranceapprovaloftheacquisitionofdomesticinsurers,(ii)priorrevieworapprovalofcertaintransactionsbetweenthedomesticinsureranditsaffiliates,and(iii)regulationofdividendsmadebythedomesticinsurer.Alltransactionswithinaholdingcompanysystemaffectingdomesticinsurersmustbedeterminedtobefairandreasonable.

AsaresultoftheNAIC’sSolvencyModernizationEffort,whichdatesbackto2008,in2014,theNAICadoptedtheCorporateGovernanceAnnualDisclosureModelAct,whichhasbeenenactedbyourleadstateofIowa,aswellasourdomesticstatesofTexasandNorthDakota.Themodellawrequiresinsurerstomakean annual confidential filing regarding their corporate governance policies. In addition, the NAICadopted the Risk Management and OwnRisk and SolvencyAssessment Model Act (“ORSA”), which also has been adopted by Iowa, Texas and North Dakota. ORSA requires insurers to maintain a risk managementframeworkandconductaninternalriskandsolvencyassessmentoftheinsurer’smaterialrisksinnormalandstressedenvironments.Manystateinsuranceholdingcompanylaws,includingthoseofIowa,TexasandNorthDakota,havealsobeenamendedtorequireinsurerstofileanannualconfidentialenterpriseriskreportwiththeirleadstateregulator,disclosingmaterialriskswithintheentireholdingcompanysystemthatcouldposeanenterpriserisktotheinsurer.

State Dividend Limitations. UnderTexasandNorthDakotalaw,respectively, AAICandAspenSpecialtymayonlypaydividendsoutofearnedsurplusasdistinguishedfromcontributedsurplus.Inaddition,underTexasandNorthDakotalaw,aninsurancecompany’spolicyholdersurplusafterpaymentofadividendmustbereasonableinrelationtoitsoutstandingliabilitiesandadequateforitsfinancialneeds.

In addition, Texas and North Dakota law generally limit the ability of AAIC or Aspen Specialty to pay dividends above a specified level, without priorregulatory approval. Dividends or distributions in excess of specified level are deemed “extraordinary” and are subject to prior notice to and approval of theapplicablestateinsuranceregulator.

Aspen U.S. Holdings, Inc. (“Aspen U.S. Holdings”) must also meet its own dividend eligibility requirements under Delaware corporate law in order todistributeanydividendsreceivedfromAAIC.Inparticular,anydividendpaidbyAspenU.S.Holdingsmustbedeclaredoutofsurplusornetprofits.

StateRisk-BasedCapitalRegulations.U.S.insurersaresubjecttorisk-basedcapital(“RBC”)guidelinesthatprovideamethodtomeasurethetotaladjustedcapital(statutorycapitalandsurplusplusotheradjustments)takingintoaccountthespecificriskcharacteristicsoftheinsurer’sinvestmentsandproducts.Therisk-basedcapitalrequirementforpropertyandcasualtyinsurersmeasures:(i)underwritingrisk,whichistheriskoferrorsinpricingandreserves;(ii)assetrisk,whichistheriskofassetdefaultforfixedassetsandloss-in-marketvalueforequityassets;(iii)creditrisk,whichistheriskoflossesfromunrecoverablereinsuranceandtheinabilityofinsurerstocollectagents’balancesandotherreceivables;and(iv)off-balancesheetrisk,whichisprimarilytheriskcreatedbyexcessivegrowth.Thecapitalrequirementsforeachriskcategoryaredeterminedbyapplyingspecifiedfactorstoassets,premiums,reservesandotheritems,withhigherfactorsforitems with greater underlying risk and lower factors for items with less risk. The formula is used by insurance regulators as an early warning tool to identifydeterioratingorweaklycapitalizedcompaniesforthepurposeofinitiatingcorrectivecompanyactionorregulatoryaction.InsurershavinglessstatutorysurplusthanrequiredbytheRBCmodelformulawillbesubjecttovaryingdegreesofregulatoryactiondependingonthelevelofcapitalinadequacy.AsofDecember31,2020,allofourU.S.insurancesubsidiariesexceededthelevelsthatwouldrequirecompanyactionorregulatoryaction.

GuarantyFundAssessmentsandResidualMarketMechanisms.Moststatesrequirelicensedinsurancecompaniestoparticipateinguarantyfundsinordertoprovidefundsforpaymentoflossesforinsurerswhichhavebecomeinsolvent.Assessmentsaregenerallybetween1%and2%ofannualpremiumwritteninthestate.Somestatesalsorequirelicensedandadmittedinsurerstoparticipateinvariousstateresidualmarketmechanismswhosegoalistoprovideaffordabilityandavailability of insurancetothoseclients whomaynot otherwisebeabletoobtaininsurance, including, for examplecatastropheinsuranceinhigh-riskareas. Iflossesexceedthefunds,thepoolisavailabletopaythoselosses.Thepoolshavetheabilitytoassessinsurerstoprovideadditionalfundstothepool.Theamountsoftheassessmentforeachcompanyarenormallybased

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upontheproportionofeachinsurer’s(andinsomecasestheinsurer’sanditsaffiliates’)writtenpremiumforcoveragessimilartothoseprovidedbythepool,andarefrequentlyuncapped.

Cybersecurity Regulations.The Gramm-Leach-Bliley Act requires financial institutions to safeguard the confidentiality and security of nonpublic personalinformation.In2017,newcybersecurityrulestookeffectforfinancialinstitutions,insurersandcertainothercompaniessupervisedbytheNewYorkDepartmentofFinancialServices(the“NYDFSCybersecurityRegulation”),suchasAAIC,whichislicensedinNewYork.TheNYDFSCybersecurityRegulationimposessignificantregulatoryrequirementsintendedtoprotecttheconfidentiality,integrityandavailabilityofinformationsystems.

In2017,theNAICalsoadoptedtheInsuranceDataSecurityModelLaw(the“CybersecurityModelLaw”).TheCybersecurityModelLawrequiresinsurers,insuranceproducersandotherentitiesrequiredtobelicensedunderstateinsurancelawstocomplywithcertainrequirementsunderstateinsurancelaws,suchasdeveloping and maintaining a written information security program, conducting risk and overseeing the data security practices of third-party vendors. TheCybersecurityModelLawcloselyresemblestheNYDFSCybersecurityRegulationandhasbeenadoptedbyseveralU.S.states.Significantothercomprehensiveprivacylawshavebeenenactedthat someofourbusinessesaresubject to, most notablytheCaliforniaConsumerPrivacyAct(CCPA),whichwentintoeffectJanuary1,2020.Severalotherstatesareconsideringadoptinglawsandregulationsimposingobligationsregardingthehandlingofpersonaldata.

Operations of Aspen U.K., Syndicate 4711 and Aspen Bermuda.Asstatedabove,AspenU.K.andSyndicate4711,areeligibletowritesurpluslinesbusinessasalien,non-admittedinsurersinall50U.S.states,theDistrictofColumbiaandotherU.S.jurisdictions.BecauseAspenU.K.andSyndicate4711arenotlicensedunderthelawsofanyU.S.state,U.S.solvencyregulationtoolsotherwiseapplicabletoadmittedinsurersdonotgenerallyapplytothem.However,AspenU.K.and Syndicate 4711 are subject to federal and state incidental regulations in areas such as those pertaining to federal and state reporting related to terrorismcoverageandpost-disasteremergencyorders.

Credit for Reinsurance. AspenU.K.andAspenBermudaalsoprovidereinsurancetoU.S.cedants.Ingeneral,aU.S.domiciledcedingcompanythatobtainsreinsurance froma reinsurer that is licensed, accredited or approvedbythe jurisdiction in whichthe cedingcompanyis domiciled is permitted to reflect in itsstatutoryfinancialstatementsacreditinanaggregateamountequaltotheliabilityforunearnedpremiumsandlossreservesandlossexpensereservescededtothereinsurer.Manyjurisdictionsalsopermitcedingcompaniestotakecreditontheirstatutoryfinancialstatementsforreinsuranceobtainedfromunlicensedornon-admitted reinsurers if certain prescribed security arrangements are made. Aspen U.K. and Aspen Bermuda have obtained approval of a multi-beneficiary trustarrangement that satisfies the credit for reinsurance requirements for their U.S. customers. Generally, the minimumtrust fund amount is $20.0 million plus anamountequalto100%ofareinsurer’s U.S.reinsuranceliabilities collateralizedunderthisarrangement. AspenBermudahasobtainedapprovaltopostreducedcollateralwithrespecttoobligationsowedtocedantsdomiciledinFlorida,NewYorkandNorthDakota(i.e.,50%versus100%).

Recent developments in U.S. and international laws are trending towards eliminating collateral requirements for alien reinsurers operating in non-domesticmarkets.TheDodd-FrankActauthorizedtheU.S.DepartmentoftheTreasuryandtheOfficeoftheU.S.TradeRepresentativetonegotiatecoveredagreementsgoverningcertainmattersrelatingtoinsurancewithforeignjurisdictions,includingreinsurancecollateral,groupsupervisionandexchangeofinformationbetweensupervisoryauthorities.Suchcoveredagreementscouldpre-emptstateinsurancelaws.Pursuanttothisauthority,inSeptember2017,theU.S.federalauthoritiesandtheE.U.signedacoveredagreementtoaddress,amongotherthings,groupsupervisionandreinsurancecollateralrequirementsand,inanticipationofBrexit,theU.S.andU.K.signedacoveredagreementinDecember2018consistentwiththeU.S.andE.U.agreement.TheU.S.alsoreleaseda“StatementoftheUnitedStates on the Covered Agreement with the European Union” (the “Policy Statement”) providing the U.S.’s interpretation of certain provisions in the E.U.agreement.Intermsofreinsurance,bothcoveredagreementseliminatecollateralandlocalpresencerequirementsforalienreinsurersthatsatisfycertaincriteria,includingbeingdomiciledina“reciprocaljurisdiction.”U.S.stateregulatorshaveuntilSeptember22,2022toadoptthereinsurancerequirementsforE.U.andU.K.reinsurersthatmeettheprescribedminimumconditionssetforthinthecoveredagreementsorstatelawimposingreinsurancecollateralrequirementsmaybesubjecttofederalpreemption.In2019theNAICadoptedadditionalrevisionstoitsCreditforReinsuranceModelLawandModelRegulation(together,the“2019Amended Credit for Reinsurance Model Act”) to conform to the reinsurance collateral elimination requirements of the covered Agreements. North Dakotacurrently has pending legislation to adopt such amendments to the credit for reinsurance model law and the NAIC has recently adopted a new accreditationstandard that requires states to adopt the revisions no later than September 1, 2022. The NAIChas approved Bermuda as a “reciprocal jurisdiction.” We willcontinuetomonitordevelopmentsincollateraleliminationwithaviewtoseekingapprovaltoeliminateAspenU.K.andAspenBermudacollateralrequirementsinthestatesandjurisdictionsthatenactthe2019AmendedCreditforReinsuranceModelAct.

DevelopingInternationalMattersandGroupCapital.InNovember2019,theInternationalAssociationofInsuranceSupervisors(IAIS)adoptedtheCommonFrameworkfortheSupervisionofInternationallyActiveInsuranceGroups

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(ComFrame). ComFrame is applicable to entities that meet the IAIS’s criteria for internationally active insurance groups (IAIGs) and are designated as such.ComFrameestablishesinternational standardsfor thedesignationof a group-widesupervisor for eachIAIGandfor theimpositionof groupsupervision, groupcapital requirements, uniform standards for insurer corporate governance, enterprise risk management and other control functions and resolution planningapplicable to an IAIG in addition to the current legal entity capital requirements imposed by relevant insurance laws and regulations. The NAIC has alsopromulgatedamendmentstotheinsuranceholdingcompanysystemmodellawthataddressessupervisionofIAIGstoallowstateinsuranceregulatorsintheU.S.tobedesignatedasgroup-widesupervisorsforU.S.-basedIAIGsoracknowledgeanotherregulatoryofficialactingasthegroupwidesupervisorofanIAIG.InNovember 2019, the IAIS also adopted a revised version of the risk-based global insurance capital standard (ICS), which is the group capital component ofComFrame. In December 2020, the NAICadopted a group capital calculation tool (“GCC”) using an RBCaggregation methodology for all entities within aninsurance holding company systemgroup, including non-U.S. entities, and is seeking effective equivalency of such tool to the ICSfor U.S.-based IAIGs. TheNAIChasalsoadoptedchangestotheinsuranceholdingcompanysystemmodellawtorequire,subjecttocertainexceptions,theultimatecontrollingpersonofeveryinsurersubjecttotheholdingcompanyregistrationrequirementtofileanannualgroupcapitalcalculationwithitsleadstateregulator.ThegoalistoprovideU.S.regulatorswithamethodtoaggregatetheavailablecapitalandtheminimumcapitalofeachentityinagroupinawaythatappliestoallgroupsregardlessoftheirstructure.ThePolicyStatementwithrespecttotheU.S.participationonthecoveredagreementsalsoprovidesthattheU.S.expectsthattheGCCwillsatisfythegroupcapitalassessmentrequirementundertheE.U.andU.K.coveredagreements.TheNAIChasstatedthatthecalculationwillbearegulatorytoolandwillnotconstitutearequirementorstandard.Itisnotpossibletopredictwhatimpactanysuchregulatorytoolmayhaveonourbusiness.

In the event that Apollo and Apollo’s insurance company affiliates become an IAIG, we may be subject to a group capital calculation consistent with orcomparabletointernationalcapitalstandardsinthatcontext.Itispossiblethatthedevelopmentoftheseinternationalstandardswillhaveanimpactonourcapitalpositionandcapitalstructureinthefuture.Wecannotpredictwithanydegreeofcertaintytheadditionalcapitalrequirements,compliancecostsorotherburdenstheserequirementsmayimposeonus.Other U.S. Regulated Entities

Investment adviser regulation. Our subsidiary Aspen Capital Advisors Inc. (“Aspen Advisors”) is registered with the SEC as a registered investmentadviser. Aspen Advisors is the investment adviser to a private investment fund that primarily invests in securities tied to weather, natural disasters or otherinsurancerisksaswellascertaincollateralizedpropertycatastrophereinsurancecontracts.Inthefuture,AspenAdvisorsmayformandmanageadditionalprivatelyofferedpooledinvestmentvehicles,customizefundsforsingleinvestorsorgroupsofinvestorsormanageseparatelymanagedaccountsofotherqualifiedclientsonalimitedbasis.AspenAdvisorsnetassetsundermanagementasatDecember31,2020were$81.9million(December31,2019—$97.3million),allofwhichweremanagedonadiscretionarybasis.TheamountdiscloseddiffersfromAspenAdvisors“regulatoryassetsundermanagement”disclosedinPart1ofitsFormADV,whichiscalculatedinaccordancewiththerequirementsofthatform.

AspenAdvisorsissubjecttoregulationasaninvestmentadviserbytheSEC.Federalandstatesecuritieslawsandregulationsareprimarilyintendedtoprotectinvestorsinthesecuritiesmarketsandgenerallygrantregulatoryagenciesbroadrulemakingandenforcementpowers,includingthepowertolimitorrestricttheconductofbusinessforfailuretocomplywithsuchlawsandregulations.TheSECandstatesecuritiesregulatoryauthoritiesfromtimetotimemaymakeinquiriesandconductexaminationsregardingcompliancebyAspenAdvisorswithsecuritiesandotherlawsandregulations.Weintendtocooperatewithsuchinquiriesandexaminationsandtakecorrectiveactionwhenwarranted. AspenAdvisorsmayalsobesubjecttosimilar lawsandregulationsinforeigncountriesif it providesinvestmentadvisoryservices,offersproductssimilartothosedescribedaboveorconductsotheractivities.

Legal Proceedings

Similartotherestoftheinsuranceandreinsuranceindustry,wearesubjecttolitigationandarbitrationintheordinarycourseofourbusiness.Oursubsidiariesareregularlyengagedintheinvestigation,conductanddefenseofdisputes,orpotentialdisputes,resultingfromquestionsofinsuranceandreinsurancecoverageorclaimsactivities.Pursuanttoourinsuranceandreinsurancearrangements,manyofthesedisputesareresolvedbyarbitrationorotherformsofalternativedisputeresolution.Insomejurisdictions,notablytheU.S.,afailuretodealwithsuchdisputesorpotentialdisputesinanappropriatemannercouldresultinanawardof“badfaith”punitivedamagesagainstourOperatingSubsidiaries.Inaddition,wemaybesubjecttolawsuitsandregulatoryactionsinthenormalcourseofbusinessthat do not arise from, or directly relate to, insurance and reinsurance coverage or claims. This category of litigation typically involves, among other things,allegationsofunderwritingerrorsoromissions,employmentclaimsorregulatoryactivity.

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Whileanylegalorarbitrationproceedingscontainanelementofuncertainty,wedonotbelievethattheeventualoutcomeofanyspecificlitigation,arbitrationoralternativedisputeresolutionproceedingstowhichwearecurrentlyapartywillhaveamaterialadverseeffectonthefinancialconditionofourbusinessasawhole.

C. Organizational Structure

TheCompany’sordinarysharesareownedbyParent, whichisanaffiliateofcertaininvestmentfundsmanagedbyaffiliatesofApolloGlobalManagement,Inc., a leading global investment manager. Class Acommonstock and certain preferred shares of Apollo Global Management, Inc. are publicly traded on theNYSE.

TheCompany’sprincipaloperatingsubsidiariesatDecember31,2020areasfollows:

Name of Subsidiary Jurisdiction of Incorporation Ownership Interest HeldAspenInsuranceUKLimited UnitedKingdom 100.0%AspenBermudaLimited Bermuda 100.0%AspenSpecialtyInsuranceCompany NorthDakota 100.0%AspenAmericanInsuranceCompany Texas 100.0%AspenUnderwritingLimited* UnitedKingdom 100.0%

*AUL(ascorporatememberofSyndicate4711whichismanagedbyAMAL)

RefertoExhibit8.1tothisreportforalistingofalltheCompany’ssubsidiaries.

D. Property, Plants and Equipment

WeleaseofficespaceinHamilton,Bermudawhereweareheadquartered.Inaddition,theCompanyanditssubsidiariesleaseofficespaceintheUnitedStates,theUnitedKingdom,Australia,SingaporeandSwitzerland.Werenewandenterintoleasesintheordinarycourseofbusinessasrequired.Formoreinformationonourleasingarrangements,refertoItem18,Note18ofourconsolidatedfinancialstatements,“OperatingLeases.”

Item 4A.Unresolved Staff Comments

Notapplicable.

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Item 5.Operating and Financial Review and Prospects

Thefollowingis a discussionandanalysis of our financial conditionandresults of operations for the twelvemonthsendedDecember 31, 2020, 2019and2018.ThisdiscussionandanalysisshouldbereadinconjunctionwithourauditedconsolidatedfinancialstatementsandrelatednotescontainedinItem18ofthisreport. The discussion belowincludes forward-looking statements, which, although based on assumptions that we consider reasonable, are subject to risks anduncertaintieswhichcouldcauseactualeventsorconditionstodiffermateriallyfromthoseexpressedorimpliedbytheforward-lookingstatements.SeeItem5G,SafeHarborbelowandItem3D,RiskFactorsofthisreportforadiscussionofrisksanduncertainties.

Executive Overview

Business Improvement Initiatives. Since2017,wehaveimplementedanumberof strategic initiatives tostrengthenthefundamentals of ourbusinessesandbetter position us to create value over the long-term. This includes the implementation of various recent initiatives following the Merger in February 2019,includingunderwritingportfolioreviewsanddecisionstowinddownbusinessthatdidnotmeetourunderwritingperformancecriteria.Wealsotookstrategicstepstoreducevolatilityintheunderwritingportfoliobyreducingcatastropheexposure.Despitethis,weincreasedgrosswrittenpremiumsto$3.7billion,in2020upfrom$3.4billionin2019,aswecontinuetoseeimprovingtradingconditionsandanimprovedrateenvironment.

During2020,wecontinuedourjourneytotransformthebusiness.Thisincludedrefocusingoninsuranceandreinsurancelinesandclassesofbusinesswherewe have the expertise, product set and market presence to generate underwriting profits across market cycles; expanding our capital markets capabilities; andcontinuingtodeployourStrategicAssetAllocation,whichisaimedatimprovingyieldsinourinvestmentportfolio.Notabletransactionsinclude:

• OnDecember14,2020wecompletedtheCGBSale,realizingagainonsaleof$8.6million.TheCGBSalewillresultinamaterialdiminutionofourU.S.agriculturalbusinessin2021andbeyond.In2020,Aspen’sU.S.agriculturalbusinessrepresented$334.8millioningrosswrittenpremium,virtuallyallofwhichwasderivedfromourrelationshipwithCGBDS.Inaddition,theCompanyenteredintoacommutationagreementwithCGBDS(the“CommutationAgreement”),underwhichwepaid$2.2milliontoCGBDSasacommutationsettlementforthe2018and2019cropyears;and• In July 2020, we sold our renewal rights to our surety insurance book of business to a third party and executed a loss portfolio transfertransactionforthetransferofprior-yearliabilities.Wecurrentlycontinuetounderwriteonlyasmallportionofsuretybusinessonafrontedbasistothepurchaserinarenewalrightstransaction,whichissubjecttoa100%quotasharereinsuranceagreementbacktothepurchaser,orviaalimitedreinsurancequotashareofthebook.

COVID-19.COVID-19meantthat2020wasayearmorechallengingthanmanyofuscanrememberwithbothprofoundhumanandeconomicconsequences.Whilethevaccineprogramgivescauseforoptimism,therecanbenodoubtsthatthepandemicwillhaveadeepandlastingimpactonbusinessandsociety.

Aspenrespondedtotheeventsoflastyear;westoodbyourclientstopayvalidclaims,continuedtoselectivelywritenewbusinesstogiveourtradingpartnerssupport andconfidence, andsawour people demonstrate admirable commitment, determination andexpertise in what were extremely trying circumstances formany.

Underlying Underwriting Performance. The company reports an overall combined ratio of 107.3%, which includes $181.2 million (7.1 combined ratiopercentage points) of losses, net of reinsurance recoverables. experienced due to COVID-19 as well as a significant catastrophe year of $179.6 million (7.1combinedratiopercentagepoints).

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For the Twelve Months Ended December 31,Business Segment 2020 2019 2018

($ in millions)ReinsuranceCatastrophes 115.3 130.8 222.2COVID-19losses 128.7 — —Total Reinsurance catastrophes 244.0 130.8 222.2

InsuranceCatastrophes 64.3 18.1 52.5COVID-19losses 52.5 — —Total Insurance catastrophes 116.8 18.1 52.5

Total Catastrophes 360.8 148.9 274.7

Improvement in the underlying performance of our portfolio is demonstrated by our accident year ex-catastrophe combined ratio, which has improvedsignificantlyto93.1%from105.0%in2019.

Repositioned Reinsurance Coverage.In2020,theCompanycontinuedtorepositioncertainofitsexternalreinsurancecoveragesarrangements,notably:• OnMarch 2, 2020, the Company entered into an adverse development cover reinsurance agreement with a subsidiary of Enstar, pursuant towhich Enstar’s subsidiary will reinsure losses incurred on or prior to December 31, 2019. Enstar’s subsidiary will provide $770.0 million of cover inexcessof$3.805billionretentionuptoanaggregateof$4.575billion,andanadditional$250.0millionofcoverinexcessabove$4.815billion,upto$5.065billion.AsaresultoftheADC,wehavesignificantlyreducedourexposuretoclaimsfromrisksunderwrittenonorpriortoDecember31,2019,andweexpecttheADCtosignificantlyreducevolatilityfromourhistoricalbusinessgoingforward.Thetransactioncompletedduringthesecondhalfof2020,followingreceiptofregulatoryapprovalsandsatisfactionofvariousotherclosingconditions;and• On January 1, 2020, the Company entered into a collateralized ceded reinsurance transaction to cover some of its casualty insurance andreinsurancelines.Thecoveragewasprovidedbyathirdpartycapitalquotashareproviderthatprovidedadvantageouscedecommissiontermscomparedwiththoseavailableintheopenmarket.

Capital Management.Wecontinuetofocusoncapitalmanagementandmaintainourstrongcapitalbase.During2020,theCompanyundertookthefollowingprincipalcapitalmanagementtransactions:

• Duringthefourthquarterof2020,ourparentcompanyHighlandsBermudaHoldco,Ltd.contributedadditionalcapitaltotaling$268.0million.

Investment Management. The Company continued its execution of its Strategic Asset Allocation program, including further diversifying its portfolio ofprivately-heldinvestments,andunwoundourremainingexposurestointerestrateswaps.

Wehavesuccessfullyreorganizedandsimplifiedouroperatingmodelaroundkeysegmentsandmadeanumberofseniorappointmentstotheleadershipteam.Atthesametime,weareworkinghardtocreateacultureatAspenthatcanattractandretaintheverybesttalent.Aspartofthiswecontinuetobuildaninclusiveenvironmentthatencouragesandempowersadiversegroupofpeople,whilealsotakingstepstoconsiderhowwecanbestmanageourimpactontheenvironmentandpositivelyaffectthecommunitiesweserve.

As we look ahead to 2021, we are well-positioned in our refocused insurance and reinsurance lines and classes of business where we have the expertise,product set andmarket presence to generate underwriting profits, andin a market that webelieve will continue to see rate momentum. Wecontinue to hold asignificantsurplusagainstourcapitalrequirements, andtogetherwithmultipleplatforms,strongdistributionandreputationfortechnicalexpertisemeanwearewellplacedtoachieveourobjectiveofbecomingatopquartilespecialty(re)insurerinthenearterm.

A. Operating Results

OurconsolidatedfinancialstatementsarepreparedinaccordancewithU.S.GAAP.Thediscussionsthatfollowincludetablesandcommentaryrelatingtoourconsolidated income statement and our segmental operating results for the twelve months ended December 31, 2020, 2019 and 2018 and should be read inconjunctionwithourauditedconsolidatedfinancialstatements

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andrelatednotescontainedinthisreport.Thisdiscussioncontainsforward-lookingstatementsthatinvolverisksanduncertaintiesandthatarenothistoricalfacts,includingstatementsaboutourbeliefsandexpectations.Ouractualresultscoulddiffermateriallyfromthoseanticipatedintheseforward-lookingstatementsasaresult of various factors, includingthosediscussedbelowandparticularly under the headings “RiskFactors,” “Business Overview”and“Cautionary StatementRegardingForward-LookingStatements”containedinItem3DandItem4,andtheExplanatoryNoteofthisreport,respectively.

Operating highlights

• Grosswrittenpremiumsof$3,703.6millionin2020,anincreaseof7.6%from2019.

• Combined ratio of 107.3% for 2020, including $360.8 million, or 14.2 percentage points of pre-tax catastrophe losses. Catastrophe losses, net ofreinsuranceand$Nilreinstatementpremiums,include$181.2millionoflossesexperiencedduetoCOVID-19(7.1combinedratiopercentagepoints)andother catastrophe losses totaling $179.6 million (7.1 combined ratio percentage points). Combined ratio of 113.9% for 2019, which included $143.2millionor6.3percentagepointsofpre-taxcatastrophelosses,netofreinsuranceand$5.7millionofreinstatementpremiums,and110.0%for2018,whichincluded$262.9million,or12.1percentagepointsofpre-taxcatastrophelosses,netofreinsuranceand$11.8millionofreinstatementpremiums.

• Non-operatingcostsin2020of$32.7millionincludes$18.2millionofseveranceandothercosts,$12.9millionofimpairmentchargesrelatedtoleaseassetsasaresultofsub-leasingcertainofficespaceand$1.6millionofamortizationofintangibleassetsandothernon-operatingexpenses.Non-operatingcosts in 2019of $125.6 million includes $103.4 million of costs related to the Merger, severance, retention andother costs,$22.2 million of expensesrelatedtotheCompany’soperatingeffectivenessandefficiencyprogram,whichincludes$12.3millionofimpairmentchargesrelatedtoleaseassetsasaresultofsub-leasingcertainofficespace.

• Interestrateswaplossesin2020of$81.1million(December31,2019—$130.2million)arisingonthefixedforfloatingrateswapswhichwereusedintheordinarycourseoftheCompany’sinvestmentsactivitiestopartiallymitigateanynegativeimpactofrisesininterestratesonthemarketvalueoftheCompany’sfixedincomeportfolio.During2020,weunwoundourremaininginterestrateswapsandexitedourcurrentposition.

• Netfavorabledevelopmentonprioryearlossreservesof$0.9million,or0.0combinedratiopoints,for2020comparedwithnetadversedevelopmentof$(59.5)million,or(2.6)combinedratiopoints,for2019andnetfavorabledevelopmentof$111.1million,or5.0combinedratiopoints,for2018.

• Netincome(loss),adjustedforpreferencesharedividends,onaverageequityof(4.3)%for2020comparedwith(12.8)%in2019and(7.7)%in2018.

Shareholders’ equity. Total shareholders’ equity increased by $272.1 million from $2,725.5 million as at December 31, 2019 to $2,997.6 million as atDecember31,2020,themostsignificantmovementsofwhichwereasfollows:

• $268.0millionadditionalcapitalcontributionfromourparentcompanyHighlandsBermudaHoldco,Ltd.;• a decrease of $88.9 million in retained earnings primarily due to a net loss of $40.1 million and the payment of $44.5 million in dividends on our

outstandingPreferenceShares;and• anincreaseof$93.0millioninothercomprehensiveincomewhichincluded$102.3millionofnetunrealizedgainsonavailableforsaleinvestments,a

$9.6millionlossinforeigncurrencytranslationanda$0.3millionnetgaininthevalueofhedgedforeignexchangecontracts.AsatDecember31,2020,ourtotalshareholders’equityincludedPreferenceShareswithatotalvalueasmeasuredbytheirrespectiveliquidationpreferencesof

$775.0millionlessissuecostsof$21.5million(2019—$775.0millionlessissuecostsof$21.5million).

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Consolidated Income Statement Twelve Months Ended December 31, 2020 December 31, 2019 December 31, 2018 ($ in millions, except for percentages)Revenues

Grosswrittenpremiums $ 3,703.6 $ 3,442.4 $ 3,446.9Netpremiumswritten 2,582.9 2,427.9 2,082.0Grosspremiumsearned 3,643.5 3,422.4 3,534.4Netpremiumsearned 2,532.6 2,293.3 2,214.7Netinvestmentincome 154.6 197.3 198.2Realizedandunrealizedinvestmentgains 98.5 97.1 110.0Otherincome 49.8 4.9 9.0TotalRevenues 2,835.5 2,592.6 2,531.9

Expenses

Lossesandlossadjustmentexpenses 1,840.8 1,679.7 1,573.0Amortizationofdeferredpolicyacquisitioncosts 465.7 412.7 371.6General,administrativeandcorporateexpenses 410.9 521.6 491.7Interestexpense 33.9 20.2 25.9Changeinfairvalueofderivatives 65.1 144.2 31.8Changeinfairvalueofloannotesissuedbyvariableinterestentities — 3.1 4.4Realizedandunrealizedinvestmentlosses 27.4 10.9 174.7Realizedlossonthedebtextinguishment — 5.5 8.6Netrealizedandunrealizedexchangelosses 12.4 11.8 3.5Otherexpenses 10.8 1.7 2.7TotalExpenses 2,867.0 2,811.4 2,687.9(Loss)fromoperationsbeforeincometax (31.5) (218.8) (156.0)Incometax(expense)/benefit (8.6) (22.9) 10.2

Net (Loss) $ (40.1) $ (241.7) $ (145.8)Ratios

Lossratio 72.7% 73.2% 71.0%Expenseratio 34.6% 40.7% 39.0%Combinedratio 107.3% 113.9% 110.0%

Fordiscussionof2018results,refertoourAnnualReportonForm10-KavailableontheinternetsitemaintainedbytheSECatwww.sec.gov.

Gross written premiums.ThefollowingtablesetsforththeoverallchangeingrosswrittenpremiumsforourtwobusinesssegmentsinthetwelvemonthsendedDecember31,2020,2019and2018: Gross Written Premiums for the Twelve Months Ended December 31,Business Segment 2020 2019 2018 ($ in millions) % change ($ in millions) % change (in millions)Reinsurance $ 1,660.8 11.8 % $ 1,485.5 (0.7) % $ 1,495.7Insurance 2,042.8 4.4 % 1,956.9 0.3 % 1,951.2Total $ 3,703.6 7.6 % $ 3,442.4 (0.1) % $ 3,446.9

____________________

Includesgrosswrittenpremiumof$334.8millionrelatedtoCGBDS(2019—$312.5million;2018—$259.7million).Grosswrittenpremiumsfor2018include$33.1millionrelatedtoAgriLogic.

Overallgrosswrittenpremiumsincreasedby7.6%in2020comparedto2019.Grosswrittenpremiumsinourreinsurancesegmentincreasedby11.8%in2020comparedto2019duetogrowthinpropertycatastrophereinsuranceduetofavorable

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pricing, casualty reinsurance predominately driven by material rate improvements in U.S. casualty lines, and other property reinsurance due to underlyingimprovementsinpricingbenefitingprorataandriskexcesslines,partiallyoffsetbyareductioninspecialtyreinsurancelinesfollowingthe2019exitofcreditandsurety lines. Gross written premiums in our insurance segment increased by 4.4%primarily due to rate improvements in both financial and professional linesinsurance and property and casualty insurance lines. Financial and professional lines insurance gross written premiums also increased as a result of our U.S.accident and health business expanding their capacity under an existing programin early 2020. Soonthereafter in March 2020following strategic reviews wedeterminedtoceaseunderwritingandstartedtowinddownthebusiness,andinanefforttomitigatetherisksassociatedwiththisprogram,insurancemanagemententeredintoa100%quotasharearrangementforthe2020portionoftheprogram.Theincreasewaspartiallyoffsetbyreductioninmarine,aviationandenergyinsurancelinesfollowingthedecisiontoceasewritingmarineandenergyliabilitybusinessin2020.

Overallgrosswrittenpremiumsin2019decreasedby0.1%comparedto2018.Grosswrittenpremiumsinourreinsurancesegmentdecreasedby0.7%in2019comparedto2018duetoreductionsinpremiumswrittenincasualtyreinsuranceandpropertycatastrophereinsurance,partiallyoffsetbyamodestincreaseinotherpropertyreinsuranceandspecialtyreinsurance.Grosswrittenpremiumsinourinsurancesegmentincreasedby0.3%in2019comparedto2018duetogrowthinfinancialandprofessionallinesinsurance,offsetbyreductionsinmarine,aviationandenergyinsuranceandpropertyandcasualtyinsurance,wherewehaveeitherpreviouslyexitedcertainlinesofbusinessorhaveplacedcertainbusinessintorunofffollowingcompletionofstrategicreviews.

Ceded written premiums. ThefollowingtablesetsforththeoverallchangeincededwrittenpremiumsforourtwobusinesssegmentsinthetwelvemonthsendedDecember31,2020,2019and2018: Ceded Written Premiums for the Twelve Months Ended December 31,Business Segment 2020 2019 2018 ($ in millions) % change ($ in millions) % change (in millions)Reinsurance $ 358.7 53.0 % $ 234.4 (25.1)% $ 312.8Insurance 762.0 (2.3) % 780.1 (25.9)% 1,052.1Total $ 1,120.7 10.5 % $ 1,014.5 (25.7)% $ 1,364.9

Totalcededwrittenpremiumsin2020increasedby$106.2millioncomparedto2019.Changesinourreinsuranceprogramdecreasedourretentionratio,whichisdefinedasnetwrittenpremiumsasapercentageofgrosswrittenpremiums,from70.5%in2019to69.7%in2020.Cededreinsurancepremiumsdecreasedforour insurance segment, primarily due to reductions in the proportion of business ceded on marine, aviation and energy insurance and property and casualtyinsurance, partiallyoffset byanincreaseintheproportionofbusinesscededonfinancial andprofessional lines. Cededreinsurancepremiumsincreasedforourreinsurance segment due to the increase in U.S. agriculture premiums written until sold during 2020, which has a high level of reinsurance protection and thepurchaseofanewquotashareprogramprotectingourcasualtyreinsurancebusinessline.

Total cededwrittenpremiumsin2019decreasedby$350.4millioncomparedto 2018, resultingin anincrease in our retentionratio from60.4%in2018to70.5%in2019.Cededreinsurancepremiumsdecreasedforourinsurancesegment,primarilyduetoreductionsintheproportionofbusinesscededonourcasualty,financial and professional lines and property quota share programs. Ceded reinsurance premiums decreased for our reinsurance segment due to reductions incessionsinpropertycatastrophereinsurance,otherpropertyreinsurance,specialtyreinsuranceandcasualtyreinsurance.

Net premiums earned. Thefollowingtablesets forththeoverall changeinnet premiumsearnedfor ourtwobusinesssegments inthetwelvemonthsendedDecember31,2020,2019and2018:

Net Premiums Earned for the Twelve Months Ended December 31,Business Segment 2020 2019 2018 ($ in millions) % change ($ in millions) % change (in millions)Reinsurance $ 1,292.1 2.9 % $ 1,255.2 (0.1) % $ 1,256.4Insurance 1,240.5 19.5 % 1,038.1 8.3 % 958.3Total $ 2,532.6 10.4 % $ 2,293.3 3.5 % $ 2,214.7

____________________

Includesnetearnedpremiumof$228.1millionrelatedtoCGBDS;(2019—$299.5million;2018—$243.6million).Netearnedpremiumsfor2018include$2.8millionrelatedtoAgriLogic.

Netpremiumsearnedincreasedby$239.3million,or10.4%,in2020comparedto2019duetoa$221.1millionincreaseingrossearnedpremiumsandan$18.2million reduction in ceded earned premiums. Net premiums earned increased by $78.6 million, or 3.5%, in 2019 compared to 2018 due to a $190.6 milliondecreaseincededearnedpremiumspartiallyoffsetbya$112.0milliondecreaseingrossearnedpremiums.

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Combined ratio.Wemonitortheratiooflossesandlossadjustmentexpenses,policyacquisitionexpensesandgeneralandadministrativeexpensestonetearnedpremium(the“combinedratio”)asameasureofrelativeperformancewherealowerratiorepresentsabetterresultthanahigherratio.ThecombinedratiosforourtwobusinesssegmentsforthetwelvemonthsendedDecember31,2020,2019and2018wereasfollows: Combined Ratios for the Twelve Months Ended December 31,Business Segment 2020 2019 2018Reinsurance 101.8% 103.1% 104.0%Insurance 104.7% 109.7% 104.0%Total 107.3% 113.9% 110.0%

__________________Thetotalcombinedratioincludestheimpactfromcorporateexpensesandnon-operatingexpenses.

The overall combined ratio for 2020 improved by 6.6 percentage points compared to 2019 due to a decrease in both the loss ratio and expense ratio. Thedecreaseinlossratiowasdueprimarilytoareductionincurrentaccidentyearlossesoffsetbyanincreaseincatastrophelosses,mainlyduetoCOVID-19.Theexpenseratiodecreasedby6.1percentagepointsduetoadecreaseinbothoperatingandnon-operatingexpenses,duetooperatingoptimizationinitiativesandthenon-recurrenceofcertaincostsassociatedwiththemergertransactionin2019.

Thecombinedratiofor2019increasedby3.9percentagepointscomparedto2018duetoanincreaseinthelossratioandexpenseratio.Theincreaseinthelossratiowasdueprimarilytoprioryearunfavorablereservedevelopmentof$59.5millionanda$24.6millionincreaseinlargelosses.Theexpenseratiofor2019increasedby1.7percentagepointsduetolowercededcommissionandanincreaseinnon-operatingexpensesassociatedwiththemergertransaction.

Losses and loss adjustment expenses.Wehavepresentedcurrentyearlossratiosadjustedfortheimpactofcatastrophelosses,whichincludeCOVID-19lossesfor2020,andprioryearreservemovementstoderivethecurrentaccidentyearlossratioexcludingcatastrophesandCOVID-19lossestoaidintheanalysisoftheunderlying performance of the business segments. Wehave defined major 2020catastrophe losses as losses associated withCOVID-19, Hurricanes Isaias andLaura, wildfires in California and other weather-related events.We have defined major 2019 catastrophe losses as losses associated with Typhoons Faxai andHagibis,HurricaneDorian,stormsinAustralia,Indianmonsoonsandotherweather-relatedevents.

TheunderlyingchangesinlossratiosbybusinesssegmentforthetwelvemonthsendedDecember31,2020,2019and2018areshowninthetablesbelow.Thecurrentyearadjustmentsrepresentcatastrophelosseventsincurredinthoseyearswhichreflectnetclaimsandreinstatementpremiumadjustments.

For the Twelve Months Ended December31, 2020

Total Loss Ratio

Prior Year ReserveMovements

Current YearAdjustments

Accident Year Loss RatioExcluding Catastrophes

Catastrophe Losses COVID -19 LossesReinsurance 74.2 % 2.8% (8.9) % (10.0)% 58.1%Insurance 71.1 % (2.8) % (5.2) % (4.2)% 58.9%Total 72.7 % — % (7.1) % (7.1)% 58.5%

For the Twelve Months Ended December 31, 2019Total Loss

Ratio Prior Year Reserve

MovementsCurrent YearAdjustments

Accident Year Loss RatioExcluding Catastrophes

Reinsurance 73.1 % 4.4 % (10.1) % 67.4 %Insurance 73.4 % (11.0) % (1.7) % 60.7 %Total 73.2 % (2.6) % (6.3) % 64.3 %

For the Twelve Months Ended December 31, 2018Total Loss

Ratio Prior Year Reserve

MovementsCurrent YearAdjustments

Accident Year Loss RatioExcluding Catastrophes

Reinsurance 73.8 % 5.5 % (17.1) % 62.2 %Insurance 67.4 % 4.5 % (5.5) % 66.4 %Total 71.0 % 5.0 % (12.1) % 63.9 %

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ForthepurposeoftheanalysisbelowwehaveincorporatedCOVID-19lossesasacatastrophelossfor2020.

Thelossratiofor2020of72.7%improvedby0.5percentagepointscomparedto2019andlossesandlossadjustmentexpensesincreasedfrom$1,679.7millionin2019to$1,840.8millionin2020.Thedecreaseinthelossratiowaslargelyduetoalowercurrentaccidentyearex-catratioof58.5%in2020comparedto64.3%in2019anda$60.4millionfavorablemovementinthelevelofprioryearreservereleases,fromstrengtheningof$59.5millionin2019toreleaseof$0.9million in 2020. Furthermore, there was a decrease in large losses of $30.4 million which was offset by a $211.9 million increase in catastrophe losses, from$148.9millionin2019to$360.8millionin2020.

Thelossratiofor2019of73.2%increasedby2.2percentagepointscomparedto2018andlossesandlossadjustmentexpensesincreasedfrom$1,573.0millionin2018to$1,679.7millionin2019.Theincreaseinthelossratiowaslargelyduetoa$170.6millionunfavorablemovementinthelevelofprioryearreservereleases, fromreleases of $111.1 million in2018 to strengthening of $59.5 million in 2019, primarily frominternational marine and energy liability products,whichweplacedinrunoff inFebruary2020. Furthermore, there wasanincrease inlargelossesof $24.6million, including$30.4millionof credit reinsurancelosses, $16.4 million of fire-related losses and $47.0 million of other large losses. These movements were partially offset by a $125.8 million decrease incatastrophelosses,from$274.7millionin2018to$148.9millionin2019.

Inthereinsurancesegment,thelossratiofor2020was74.2%comparedto73.1%in2019largelyduetoanincreaseincatastrophelossesof$113.2millionandan$18.8milliondecreaseinreservereleases,offsetbyalowercurrentyearaccidentexcatratioof58.1%in2020incomparisonto67.4%in2019,anda$54.9milliondecreaseinlargelosses.In2020,therewere$244.0millionofcatastrophelosses,netofreinsurancerecoveries,including$128.7millionoflossesfromCOVID-19,$35.3millionfromHurricaneLaura,$9.5millionfromCaliforniaWildfires,$4.7millionfromHurricaneIsaias,and$65.8millionofotherweather-relatedevents.In2019,weexperienced$130.8millionofcatastrophelosses,netofreinsurancerecoveries,associatedwithTyphoonsHagibisandFaxai,HurricaneDorian,stormsinAustralia,Indianmonsoonsandotherweather-relatedevents.

Intheinsurancesegment,thelossratiofor2020was71.1%comparedto73.4%in2019.Thedecreaseinthelossratioin2020wasprimarilyduetoa$79.2milliondecreaseinreservestrengthening,from$114.4millionstrengtheningin2019to$35.2millionstrengtheningin2020,increaseinnetearnedpremiumsof$202.4 million, offset by $24.5 million increase in large losses and a $98.7 million increase in catastrophe losses. In 2020, the insurance segment experienced$116.8millionofcatastrophelosses,netofreinsurancerecoverables,dueto$52.5millionfromCOVID-19losses,and$64.3millionfromotherweather-relatedevents.Largelossesexperiencedduring2020included$49.2millionoffire,propertydamage,constructionandcreditriskrelatedlosses.

Thelossratiofor2019was73.4%comparedto67.4%for2018mainlyduetoa$157.1milliondecreaseinreservereleasesfroma$42.7millionreleasein2018toa$114.4millionstrengtheningin2019anda$5.0millionincreaseinlargelosses.Thesemovementsmorethanoffsettheimpactfroma$79.8millionincreasein net earned premiums. In 2019, our insurance segment experienced $18.1 million of catastrophe losses associated with Hurricane Dorian and other weather-relatedevents.

Overall,prioryearreservereleasestotaled$0.9millionin2020,comparedwithnetunfavorablereservedevelopmentof$59.5millionin2019.Reservereleasesin the reinsurance segment in 2020were $36.1 million compared to $54.9 million in 2019andcameprimarily fromcasualty reinsurance, property catastrophereinsuranceandspecialtyreinsurance,partiallyoffsetbystrengtheningonotherpropertyreinsurancelines.Netunfavorablereservedevelopmentintheinsurancesegmentin2020was$35.2millioncomparedtonetunfavorablereservedevelopmentof$114.4millionin2019andcameprimarilyfrompropertyandcasualtyinsurancelines.

Overall, prior year reserve releases in 2019 decreased by $170.6 million from$111.1 million in 2018 to $59.5 million. Reserve releases in the reinsurancesegmentin2019were$54.9millionandcamefrompropertycatastrophereinsurance,otherpropertyreinsuranceandspecialtyreinsurancelinespartiallyoffsetbyunfavorable development on casualty reinsurance. Reserve strengthening in the insurance segment in 2019 was $114.4 million compared to releases of $42.7million in 2018 and came primarily from international marine and energy liability products, which we placed in runoff in February 2020, and unfavorabledevelopmentonU.S.primarycasualtylines.Furtherinformationrelatingtothereleaseofreservescanbefoundbelowunder“—ReservesforLossesandLossAdjustmentExpenses—PriorYearLossReserves.”

Expenses.Wemonitortheratioofexpensestogrossearnedpremium(the“grossexpenseratio”)asameasureofthecosteffectivenessofouramortizationofdeferredpolicyacquisitioncosts,general,administrativeandcorporateexpenses.Thetablesbelowpresentthecontributionoftheamortizationofdeferredpolicyacquisitioncostsandgeneral,administrativeand

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corporateexpensestothegrossexpenseratiosandthetotalnetexpenseratiosforthetwelvemonthsendedDecember31,2020,2019and2018.Wealsopresenttheeffectofreinsurancepurchasedwhichimpactsthereportednetexpenseratiobyexpressingtheexpensesasaproportionofnetearnedpremiums.

For the Twelve Months Ended December 31, 2020Ratios Based on Gross Earned Premium Reinsurance Insurance Total

Grosspolicyacquisitionexpenseratio 18.0 % 20.8 % 19.5%Effectofcededreinsurance 1.0 % (3.1) % (1.1)%Netpolicyacquisitionexpenseratio 19.0 % 17.7 % 18.4%

Grossgeneral,administrativeandcorporateexpenseratio 6.9 % 9.7 % 11.3%Effectofcededreinsurancepremiums 1.7 % 6.2 % 4.9%Netgeneralandadministrativeexpenseratio 8.6 % 15.9 % 16.2%

Totalnetexpenseratio 27.6 % 33.6 % 34.6%

For the Twelve Months Ended December 31, 2019Ratios Based on Gross Earned Premium Reinsurance Insurance Total Grosspolicyacquisitionexpenseratio 19.4 % 20.0 % 19.8%Effectofcededreinsurance 1.7 % (5.8) % (1.8)%Netpolicyacquisitionexpenseratio 21.1 % 14.2 % 18.0%

Grossgeneral,administrativeandcorporateexpenseratio 7.5 % 11.9 % 15.2%Effectofcededreinsurancepremiums 1.4 % 10.2 % 7.5%Netgeneral,administrativeandcorporateexpenseratio 8.9 % 22.1 % 22.7%

Totalnetexpenseratio 30.0 % 36.3 % 40.7%

For the Twelve Months Ended December 31, 2018Ratios Based on Gross Earned Premium Reinsurance Insurance Total Grosspolicyacquisitionexpenseratio 19.1 % 19.1 % 19.1%Effectofcededreinsurance 1.7 % (7.5) % (2.3)%Netpolicyacquisitionexpenseratio 20.8 % 11.6 % 16.8%

Grossgeneral,administrativeandcorporateexpenseratio 7.4 % 12.3 % 13.9%Effectofcededreinsurancepremiums 2.0 % 12.7 % 8.3%Netgeneral,administrativeandcorporateexpenseratio 9.4 % 25.0 % 22.2%

Totalnetexpenseratio 30.2 % 36.6 % 39.0%

____________________

Thetotalgroupgeneralandadministrativeexpenseratioincludescorporateandnon-operatingexpenses.

Netpolicyacquisitionexpensesincreasedby$53.0millionin2020comparedto2019andby$41.1millionin2019comparedto2018primarilyasaresultofincreasedgrossandcededwrittenpremiums.

Thedecrease in the gross policy acquisition expense ratio from19.8%in 2019to 19.5%in 2020wasdueto a changein the mixof business written in theinsurancesegment,anddecreasedprofitcommissiononcertaincontractswithinthereinsurancesegment.

General,administrative,corporateandnon-operatingexpensesdecreasedby$110.7millionfrom$521.6millionin2019to$410.9millionin2020.Thegrossgeneral,administrativeandcorporateexpenseratioin2020decreasedby3.9percentage

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pointscomparedtothepriorperiodprimarilyduetoa$92.9milliondecreaseinothernon-operatingcosts,$33.5millionreductioninoperatingexpenses,partiallyoffsetbyanincreaseincorporatecosts.

Non-operating costs in 2020totaling $32.7 million includes $18.2 million severance, retention awards and other costs, $12.9 million of impairment chargesrelatedtoleaseassetsasaresultofsub-leasingcertainofficespaceand$1.6millionofamortizationofintangibleassetsandothernon-operatingexpenses.

Non-operatingcostsin2019totaling$125.6millioninclude$103.4millionofexpensesrelatedtotheMerger,severance,retentionandothercosts,and$22.2millionofexpensesrelatedtoouroperationaleffectivenessandefficiencyprogram,whichincludes$12.3millionofimpairmentchargesrelatedtoleaseassetsasaresultofsub-leasingcertainofficespace.

Net other income. In2020,weearnedotherincomeof$49.8million(2019—$4.9million),whichincludedagainonthesaleofourrenewalrightstooursuretyinsurancebookofbusinesstoathirdparty,totaling$43.1million,partiallyoffsetbyotherexpensestotaling$10.8million(2019—$1.7million).

Investment gains.Total net realizedandunrealizedinvestment gainsfor thetwelvemonthsendedDecember31, 2020were$71.1million(2019—gainsof$86.2million),drivenprimarilybymarktomarketgainsinourfixedincomeportfolios.

Net investment income. In2020,wegeneratednetinvestmentincomeof$154.6million, adecreaseof21.6%fromtheprioryear(2019—$197.3million),largely as a result of redeploying $770.0 million of the investment portfolio to the adverse development cover. Net investment income in 2020 is comprisedprimarilyofinterestonourfixedincomesecuritiesportfolio.

Change in fair value of derivatives.Inthefirstquarterof2019,theCompanyenteredintofixedforfloatinginterestrateswapswithatotalnotionalamountof$3,138.0 million due to mature between January 18, 2021 and January 18, 2034. The interest rate swaps were used in the ordinary course of the Company’sinvestmentsactivitiestopartiallymitigateanynegativeimpactofrisesininterestratesonthemarketvalueoftheCompany’sfixedincomeportfolio.During2020,we unwound the remaining $1,800.0 million of our interest rate swaps. For the twelve months ended December 31, 2020, there was a loss of $81.1 million(December31,2019—$130.2million).

Weuseforeignexchangecontractstomanageforeigncurrencyrisk.Aforeignexchangecontractinvolvesanobligationtopurchaseorsellaspecifiedcurrencyat a future date at a price set at the time of the contract. Foreign exchange contracts will not eliminate fluctuations in the value of our assets and liabilitiesdenominatedinforeigncurrencies,butratherallowustoestablisharateofexchangeforafuturepointintime.

As at December 31, 2020, we held foreign exchange contracts that were not designated as hedging under ASC815 - “Derivatives and Hedging”with anotionalamountof$1,402.3million(2019—$1,696.3million).Theforeignexchangecontractsarerecordedasderivativesatfairvalueinthebalancesheetwithchangesrecordedasachangeinfairvalueofderivativesinthestatementofoperations.ForthetwelvemonthsendedDecember31,2020,theimpactofforeignexchangecontractsonnetincomewasagainof$16.0million(December31,2019—lossof$14million).

AsatDecember31,2020,weheldforeignexchangecontractsthatweredesignatedashedgingunderASC815withanotionalamountof$90.6million(2019—$85.5million).Theforeignexchangecontractsarerecordedasderivativesatfairvaluewiththeeffectiveportionrecordedinothercomprehensiveincomeandtheineffectiveportionrecordedasachangeinfairvalueofderivativesinthestatementofoperations.Thecontractsareconsideredtobeeffectiveandthereforethemovementinothercomprehensiveincomerepresentingtheeffectiveportionwasreflectedasagainof$0.3millionforthetwelvemonthsendedDecember31,2020(December31,2019—gainof$4.8million).

Astheforeignexchangecontractssettle,therealizedgainorlossisreclassifiedfromothercomprehensiveincomeintogeneral,administrationandcorporateexpensesofthestatementofoperationsandothercomprehensiveincome.ForthetwelvemonthsendedDecember31,2020,theamountrecognizedwithingeneral,administration and corporate expenses for settled foreign exchange contracts was a realized loss of $3.2 million (December 31, 2019 —gain of $0.9 millionrecognizedwithingeneral,administrationandcorporateexpenses).

Thechangeinfairvalueofderivativesin2020wasattributabletofixedforfloatinginterestrateswapsthathadalossof$81.1million(2019—lossof$130.2million),whichwaspartlyoffsetbyagainonforeignexchangecontractsof$16.0million(2019—lossof$14.0million).

Interest expense.Interestexpenseof$33.9millionistheinterestdueonthe2023SeniorNotestogetherwith$19.6millioninterestpaidondeferredpremiumpaymentsforanadversedevelopmentcover.TheincreaseintheinterestchargeinthetwelvemonthsendedDecember31,2019wasduetotheinterestpayableondeferredpremiumpaymentsontheadversedevelopmentcoverreinsuranceagreementoffsetbytheredemption,onSeptember30,2019,of$125.0millionofour6.00%SeniorNotesdue2020.

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Income (loss) before tax.InthetwelvemonthsendedDecember31,2020,lossbeforetaxwas$31.5million(2019—lossof$218.8million),consistingoftheamountssetoutinthetablebelow:

For the Twelve Months EndedDecember 31, 2020 December 31, 2019 December 31, 2018

($ in millions)Underwriting(loss) $ (81.9) $ (140.6) $ (87.6)Corporateexpenses (70.2) (54.5) (56.8)Non-operatingexpenses (32.7) (125.6) (77.2)Netotherincome 39.0 3.2 6.3Netinvestmentincome 154.6 197.3 198.2Changeinfairvalueofderivatives (65.1) (144.2) (31.8)Changeinfairvalueofloannotesissuedbyvariableinterestentities — (3.1) (4.4)Realizedandunrealizedinvestmentgains 98.5 97.1 110.0Realizedandunrealizedinvestmentlosses (27.4) (10.9) (174.7)Realizedlossonthedebtextinguishment — (5.5) (8.6)Netrealizedandunrealizedforeignexchange(losses) (12.4) (11.8) (3.5)Interestexpense (33.9) (20.2) (25.9)

(Loss)beforetax $ (31.5) $ (218.8) $ (156.0)

The improvement in underwriting result in 2020 compared to 2019 was due to an increase in gross earned premium, an improved current accident yearexcludingcatastrophelossesresult,andloweroperatingandnon-operatingexpenses.Thedecreaseinunderwritingincomein2019comparedto2018wasduetoanincreaseinlargelossesandprioryearreservedevelopment.

Theincreaseincorporateexpensein2020comparedto2019wasduetohigherstaffcosts,increasedconsultingandothercorporateexpenses.Non-operatingexpenses have decreased significantly in 2020 compared to 2019 as the Company has finally embedded the transformational changes fromthe merger and itsoperational effectiveness and efficiency program. The results from these initiatives can be seen as the Group’s general and administrative expense ratio hasdecreasedfrom22.7%in2019to16.2%in2020.

Non-operating expenses in 2020 totaling $32.7 million includes $18.2 million of severance, retention awards and other costs, $12.9 million of impairmentchargesrelatedtoleaseassetsasaresultofsub-leasingcertainofficespaceand$1.6millionofamortizationofintangibleassetsandothernon-operatingexpenses.

Theincreaseincorporateandnon-operatingexpensesin2019comparedto2018waslargelyduetoa$34.3millionincreaseinothernon-operatingcosts.Non-operatingexpensesin2019totaling$125.6millionincludes$103.4millionofcostsrelatedtotheMerger, severance, retentionandothercosts$22.2millionofexpensesrelatedtotheCompany’soperatingeffectivenessandefficiencyprogram,whichincludes$12.3millionofimpairmentchargesrelatedtoleaseassetsasaresultofsub-leasingcertainofficespace.

Realized loss on debt extinguishment. OnJune18,2018,weredeemed$125.0millioninaggregateprincipalamountofthe2020SeniorNoteswhichresultedinarealizedloss,ormake-wholepayment,of$8.6million.

OnSeptember30,2019,weredeemedtheremaining$125.0millionofour20206.00%SeniorNotesresultinginarealizedloss,ormake-wholepaymentof$5.5million.

AsatDecember31,2020,AspenHoldings’onlymaterialdebtoutstandingwasour$300million4.650%SeniorNotesdue2023(the“2023SeniorNotes”).

Change in fair value of loan notes issued by variable interest entities.TherewerenoloannotesoutstandingsinceitscommutationonJuly1,2019andthereforewerecognizedazerochangeinfairvalueofloannotes.The$3.1millionchangeinthevalueoftheloannotesin2019representstheproportionofprofitgeneratedbySilvertonattributabletothird-partyinvestors.

Income tax expense.TherewasanincometaxexpenseforthetwelvemonthsendedDecember31,2020of$8.6millionaswellasanincometaxexpenseof$22.9 million in 2019. The effective tax rate (defined as the tax charge or credit, divided by the profit or loss before tax), for the twelve months endedDecember31,2020onourlossbeforetaxwas(27.3)%(2019—(10.5)%),

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TheeffectivetaxrateissubjecttorevisioninfutureperiodsifcircumstanceschangeanddependsontherelativeprofitabilityofthebusinessunderwritteninBermuda(wheretherateoftaxoncorporateprofitsiszero),theUnitedKingdom(wherethecorporationtaxrateiscurrently19%)andtheUnitedStates(wherethefederalincometaxrateiscurrently21%).Thetaxineachoftheyearsisrepresentativeofthegeographicspreadofourbusinessbetweentaxableandnon-taxablejurisdictionsinsuchyears.

Net (loss) after tax. Wereportedanetlossaftertaxesof$40.1millionin2020comparedtoanetlossof$241.7millionin2019.Thedifferenceinnetlosswasprimarilyduetothe$58.7millionimprovementintheunderwritingresult,areductioninnon-operatingexpensesof$92.9millionandtheincreaseinotherincomeduetothegainonthesaleofourrenewalrightstooursuretyinsurancebookofbusinesstoathirdparty,totaling$43.1million.Thenetlossof$241.7millionin2019comparedtothenetlossof$145.8millionin2018wasprimarilyasaresultofunfavorablemovementinthelevelofprioryearreservereleases,adecreaseinunderwritingincomeandanincreaseinlargelosses.

Other comprehensive income.Total other comprehensive incomeincreased by $93.0 million (2019—$130.5 million increase), net of taxes, for the twelvemonths endedDecember 31, 2020. Theincrease in total other comprehensive incomeincludes a net unrealized gain of$169.4millionintheavailable for saleinvestmentportfolio(2019—$158.1millionnetunrealizedgain)largelyattributabletotheimpactoffallinginterestratesonourbondportfolios,a$67.1millionreclassification of net realized gains to net income (2019 — $6.8 million reclassified realized gains), a $0.3 million unrealized gain (2019 — $4.0 millionunrealizedgain)onthehedgedderivativecontractsandanunrealizedlossinforeigncurrencytranslationof$9.6million(2019—$24.8millionunrealizedloss)largelyattributabletotheimpactfromthecontinuedstrengtheningoftheU.S.dollar.

Recent Developments

TheglobalspreadofCOVID-19,andthegovernmentalandregulatoryactionstakentomitigateit’seffects,haveledtosignificantandongoingeconomicandsocietal disruption, includingsignificant market volatility. Ourbusiness andresults havebeenadverselyaffectedbytheCOVID-19crisis in thetwelvemonthsendedDecember 31, 2020. In our Insurance business, wehaveassessedpotential exposures in our accident andhealth line, whichwestarted to winddowninMarch 2020, as well as our ongoing operations in property, marine and energy, and casualty lines. In our Reinsurance business, we have assessed potentialexposuresfromcontingency(eventcancellation), propertyandcasualtylines.WhetherlossesassociatedwiththeCOVID-19crisiscouldtriggercoverageunderpoliciesthatwewrite,however,isdependentonspecificpolicylanguage,termsandexclusionsineachcase.

Of our total losses for the twelve months ended December 31, 2020, $181.2 million is directly associated with the COVID-19 crisis, net of reinsurancerecoverables(whichwehaveestablishedreservesfor,asignificantportionofwhichareIBNRreservesinrespectofIBNRlosses),approximately70%and30%wereattributabletoourReinsuranceandInsurancebusinesses,respectively.

However,thelevelofCOVID-19infectionscontinuestoriseincertaincountriesandthethreatofnewoutbreaksandnewstrainsofthevirusstilllooms.Manyoftheeffectsresultingfromsuchoutbreaksarestill activeordevelopingand,assuch,it isnotpossibleatthistimetoprovideadefinitiveestimateofultimatepotential insurance,reinsuranceorinvestmentexposuresoranyothereffectstheCOVID-19crisismayhaveonourresultsofoperations, financial conditionorliquidity. Accordingly, any assessment as to underwriting or investment exposure which we make at this time represents our current best estimates based onactuarial,reservingandinvestmentmanagementprocessandmaybesubjecttosignificantfurthervariationoramendmentascircumstancesdeveloporoutcomesbecome clearer. See “Risk Factors —Risks Relating to Recent Developments —The coronavirus pandemic and the responses thereto have already adverselyaffectedourbusinessandoperations,andtheultimateeffectsthereofonourbusiness,ouroperationsandourfinancialconditionandresultsofoperationsremainhighlyuncertainandimpossibletopredict.

Strategic Initiatives

Sale of Ownership Interest in Crop Re:

OnDecember14,2020wecompletedthesaleofour23.2%interestinCropRetoCGBDS(the“CGBSale”).TheCGBSalehasandwillresultinamaterialdiminutionofourU.S.agriculturalbusinessin2021andbeyond.AsapartoftheCGBSale,CGBDSpaidAAIC$71.1millionforitsownershipinterestinCropReresultinginan$8.6milliongainrecognizedwithinrealizedinvestmentgains,aswellas$14.5milliontosettlelosscarryforwardsforthe2018and2019cropyears which were recognized within policy acquisition costs. In addition, AAIC entered into a commutation agreement with CGB DS (the “CommutationAgreement”),underwhichAAICpaid$2.2milliontoCGBDSasacommutationsettlementforthe2018and

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2019cropyears.TheCommutationAgreementdoesnotcoverthecropyearsfrom2010to2017orthe2020cropyear,thereforeweremainexposedtoreinsuranceobligationsandpotentialclaimsinregardstothoseyears.

In2020,Aspen’sU.S.agriculturalbusinessrepresented$334.8millioningrosswrittenpremium,$228.1millioninnetearnedpremiumandcontributed$8.7million towards the Group’s net income. Virtually all of which was derived from our relationship with CGBDS. This business has been included within ourreinsuranceLegacyLines.

Surety Insurance Business:

In July 2020, wesold our renewal rights to our surety insurance bookof business to a third party and executed a loss portfolio transfer transaction for thetransferofprior-yearliabilities.Werecognizedagainof$43.1milliononthistransactionwhichhasbeenincludedwithinotherincomeinthefinancialstatements.Wecurrentlycontinuetounderwriteonlyasmallportionofsuretybusinessonafrontedbasistothepurchaserinarenewalrightstransaction,whichissubjecttoa100%quotasharereinsuranceagreementbacktothepurchaser,orviaalimitedreinsurancequotashareofthebook.ThisbusinesshasbeenincludedwithinourinsuranceLegacyLines.

Sale of Investment in BeneAssicurazioni(“Bene”):

OnNovember20,2020wecompletedthesaleofBenefor$6.1millionrealizingagainondisposalof$1.8million.

Adverse Development Cover Reinsurance Agreement:

On March 2, 2020, the Company announced that certain subsidiaries of the Company entered into an adverse development cover reinsurance agreement(“ADC”)withasubsidiaryofEnstar,pursuanttowhichEnstar'ssubsidiarywillreinsurelossesincurredonorpriortoDecember31,2019.Enstar’ssubsidiarywillprovide$770.0millionofcoverinexcessof$3.805billionretention,andanadditional$250.0millionofcoverinexcessabove$4.815billion.ThetransactioncompletedinSeptember2020,followingsatisfactionofvariousotherclosingconditionsandregulatoryapproval.

Carbon Syndicate:

InJune,AspenUnderwritingLimited(“AUL”)utilizeditsFundsatLloyd’stosupportCarbonSyndicate4747(“CarbonSyndicate”).Thiswasamid-yearpre-emption for a new start up syndicate. The capacity for Carbon Syndicate is £11.7 million ($16.0 million) and AUL has a 60% participation for the 2020underwritingyear(thishasbeensubsequentlysigneddownto56.09%forthe2021underwritingyear).

Interest Rate Swaps.

In the first quarter of 2019, the Companyentered into fixedfor floating interest rate swapswith a total notional amountof $3,138.0millionduetomaturebetweenJanuary18, 2021andJanuary18, 2034. Theinterest rate swapswereusedin theordinary course of the Company’s investments activities to partiallymitigate any negative impact of rises in interest rates on the market value of the Company’s fixed incomeportfolio. During 2020, weunwoundthe remaining$1,800.0millionofourinterestrateswaps.ForthetwelvemonthsendedDecember31,2020,therewasalossof$81.1million(December31,2019—$130.2million).

Investment Portfolio:

Ourresultsofoperationshavebeenimpactedbythetransferof$770.0millionincashtoEnstaraspaymentfortheADCpremium.Ourinvestmentportfoliocorrespondinglywasreducedbythatamount.

Capital:

Duringthefourthquarterof2020,ourparentcompanyHighlandsBermudaHoldco,Ltd.contributedadditionalcapitaltotaling$268.0million.

Lloyd’s EEA Insurance Policies:OnDecember30,2020,theCompanytransferreditsEEAinsurancepolicies(andrelatedliabilities)underwrittenbytheCompany’ssyndicatestoLloyd’s

InsuranceCompanyS.A.(“Lloyd’sBrussels”)pursuanttoPartVIIoftheFinancialServicesandMarketsAct2000(“PartVII”).Onthesamedate,theCompanyenteredintoa100%QuotaShareReinsuranceAgreementwherebyLloyd’sBrusselsreinsuredallrisksonthesamepoliciesbacktotheCompany.ThepurposeofthesetransactionsweretoensurethesepoliciescouldbeservicedafterBrexitonDecember31,2020.

The value of the net liabilities transferred was $72.9 million. The Company transferred cash of the same amount to Lloyd’s Brussels. Lloyd’s BrusselssubsequentlyreinsuredthesameliabilitiesbacktotheCompanyonthesameday.Thereinsurancepremiumreceivedwasofthesameamountof$72.9million.Therewasnogainorlossarisingoneithertransaction.

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BoththecashtransferredforthePartVIItransferandthepremiumsubsequentlyreceivedbackfromLloyd’sBrusselshavebeenincludedingrosswrittenpremiums.Thetransactionhasnoimpactonequity.

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Underwriting Results by Business Segment

Weareorganizedintotwobusinesssegments,namelyreinsuranceandinsurance.Wehavedeterminedourreportablesegments,ReinsuranceandInsurance,bytaking into account the manner in which management makes operating decisions and assesses operating performance. Profit or loss for each of the businesssegments is measured by underwriting profit or loss. Underwriting profit is the excess of net earned premiums over the sum of losses and loss expenses,amortizationofdeferredpolicyacquisitioncostsandgeneralandadministrativeexpenses.Underwritingprofitorlossprovidesabasisformanagementtoevaluatethesegment’sunderwritingperformance.

Managementmeasuressegmentresultsonthebasisofthecombinedratio,whichisobtainedbydividingthesumofthelossesandlossexpenses,amortizationof deferred policy acquisition costs and operating and administrative expenses by net premiums earned. Other than corporate expenses, indirect operating andadministrativeexpensesareallocatedtobusinesssegmentspredominantlybasedoneachsegment’sproportionalshareofgrossearnedpremiums.

Non-underwriting disclosures. Weprovideadditional disclosuresforcorporateandother(non-operating) incomeandexpenses. Corporateandotherincomeandexpensesincludenetinvestmentincome,netrealizedandunrealizedinvestmentgainsorlosses,expensesassociatedwithmanagingtheAspenGroup,certainstrategic and other costs, changes in fair value of derivatives and changes in fair value of loan notes issued by variable interest entities, interest expense, netrealizedandunrealizedforeignexchangegainsorlossesandincometaxes,whicharenotallocatedtothebusinesssegments.Corporateexpensesarenotallocatedtoourbusinesssegmentsastheytypicallydonotfluctuatewiththelevelsofpremiumswrittenandarenotdirectlyrelatedtooursegmentoperations.

Wedonotallocateourassetsbybusinesssegmentasweevaluateunderwritingresultsofeachsegmentseparatelyfromtheresultsofourinvestmentportfolio.Segment profit or loss for each of our business segments is measured by underwriting profit or loss. Refer to Item 18, Note 3 of our consolidated financialstatements,“SegmentReporting”forinformationongrossandnetpremiumswrittenandearned,underwritingresults,andcombinedratiosandreservesforeachofourbusinesssegments.

Reinsurance

Ourreinsurancesegmentconsistsofpropertycatastrophereinsurance, otherpropertyreinsurance, casualtyreinsuranceandspecialtyreinsurance. Foramoredetaileddescriptionofthissegment,refertoItem4,“BusinessOverview—BusinessSegments—Reinsurance”andItem18,Note3ofourconsolidatedfinancialstatements,“SegmentReporting.”

Gross written premiums.ThetablebelowshowsourgrosswrittenpremiumsforeachlineofbusinessinourreinsurancesegmentforthetwelvemonthsendedDecember31,2020,2019and2018andthepercentagechangeingrosswrittenpremiumsforeachlineofbusiness: For the Twelve Months Ended December 31,Lines of Business 2020 2019 2018 ($ in millions) % change ($ in millions) % change ($ in millions)Propertycatastrophereinsurance $ 312.0 25.0 % $ 249.6 (5.0)% $ 262.8Otherpropertyreinsurance 399.8 12.0 % 356.9 3.2% 346.0Casualtyreinsurance 394.4 33.8 % 294.7 (10.2)% 328.1Specialtyreinsurance 554.6 (5.1) % 584.3 4.6% 558.8

Total $ 1,660.8 11.8 % $ 1,485.5 (0.7)% $ 1,495.7

Theincreaseingrosswrittenpremiumsin2020comparedto2019inpropertycatastrophereinsurancewasprimarilyduetorateincreases.Theincreaseingrosswrittenpremiumsinotherpropertyreinsurancewasprimarilyduetounderlyingimprovementsinpricingbenefitingprorataandriskexcesslinestogetherwith favorable adjustment premiums. The increase in gross written premiums in casualty reinsurance was primarily due to material rate improvements in U.S.casualtylinesandfavorableadjustmentpremiums.Thedecreaseingrosswrittenpremiumsinspecialtyreinsurancewasprimarilyduetothe2019exitofcreditandsuretylinesandareductioninmortgagebusinesslines.

Thedecreaseingrosswrittenpremiumsin2019comparedto2018inpropertycatastrophereinsurancewasduetoportfoliooptimization. Theincreaseingrosswrittenpremiumsinotherpropertyreinsurancewasduetoanincreaseinpropertyfacultativeandproratapremiums.ThedecreaseingrosswrittenpremiumsincasualtyreinsurancewasduetoreductionsinU.S.casualtyreinsurancepremiums.TheincreaseingrosswrittenpremiumsinspecialtyreinsurancewaslargelyduetoincreasesinmortgageandU.S.agriculturalreinsurancebusiness,partiallyoffsetinareductionincreditandsuretyreinsurancebusiness,whichduring2019weexitedaftersellingourrenewalrightstoathirdparty.

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Ceded written premiums.Totalcededwrittenpremiumsin2020were$358.7million,anincreaseof$124.3millioncomparedto2019.TheincreaseincededwrittenpremiumswasduetotherecognitionofU.S.agriculturepremiumswhichhaveahighlevelofreinsuranceprotectionandthepurchaseofanewquotashareprogramprotectingourcasualtyreinsurancebusinessline.

Totalcededwrittenpremiumsin2019were$234.4million,adecreaseof$78.4millioncomparedto2018.Thedecreaseincededwrittenpremiumsisduetoreductionsincessionsinpropertycatastrophereinsurance,otherpropertyreinsurance,specialtyreinsuranceandcasualtyreinsurance.

Net premiums earned.Netpremiumsearnedincreasedby$36.9million,or2.9%,in2020comparedto2019largelyduetogrowthinourpropertycatastrophereinsuranceandotherpropertyreinsurance,partiallyoffsetbyareductioninspecialtyreinsurance.Netpremiumsearneddecreasedby$1.2million,or0.1%,in2019comparedto2018largelyduetodecreasedgrossearnedpremiumsfromourspecialtyreinsuranceandpropertycatastrophebusinesslines,offsetbydecreasedcededcosts.

Losses and loss adjustment expenses.Thelossratiowas74.2%in2020,anincreaseof1.1percentagepointscomparedto73.1%in2019.Theincreaseinthelossratio wasmainlyduetoanincreaseincatastrophelossesof $113.2millionandan$18.8milliondecreaseinreservereleases, offset bylowercurrent yearaccidentex-catratioof58.1%in2020incomparisonto67.4%in2019,anda$54.9milliondecreaseinlargelosses.

In 2020, our reinsurance segment experienced $244.0 millionof catastrophe losses, net of reinsurance recoveries, including$128.7 million of losses fromCOVID-19,$35.3millionfromHurricaneLaura,$9.5millionfromCaliforniawildfires,$4.7millionfromHurricaneIsaiasand$65.8millionfromotherweather-relatedevents.Largelossesexperiencedinourreinsurancesegmentduring2020were$14.3million,comprisedof$1.6millionofaviationlosses,$4.1millionoffire-relatedlosses,$1.6millionofwaterdamage-relatedlossesand$7.0millionofbusinessinterruptionlossesunrelatedtoCOVID-19.

Thelossratioin2019decreasedto73.1%comparedto73.8%in2018.Thedecreaseinthelossratiowasmainlyduetoa$91.4milliondecreaseincatastrophelosseswhichoffseta$19.6millionincreaseinlargelossesanda$13.5milliondecreaseinreservereleases.In2019,ourreinsurancesegmentexperienced$130.8millionofcatastrophelosses,netofreinsurancerecoveries,including$42.2millionfromTyphoonHagibis,$33.5millionfromTyphoonFaxai,$8.6millionfromother HurricaneDorian, $4.6million fromstormsin Australia, $3.4million fromIndianmonsoonsand$38.5millionfromother weather-related events. Largelossesexperiencedduring2019included$30.4millionofcreditreinsurancelosses,$16.4millionoffire-relatedlosses,$7.8millionofaviationlosses,$8.3millionofsatellite-relatedlossesand$6.3millionofbloodstocklosses.

Prioryearreservereleasestotaled$36.1millioninthecurrentperiodcomparedwith$54.9millioninthetwelvemonthsendedDecember31,2019.Reservereleasesin2020wereprimarilyfromcasualtyreinsurance,propertycatastrophereinsuranceandspecialtyreinsurance,partiallyoffsetbystrengtheningonotherpropertyreinsurancelines.Thereservereleasesin2019wereprimarilyduetoareductioninreservereleasesinourpropertycatastrophereinsurance,strengtheningincasualtyreinsurancebusinesslines,partiallyoffsetbyanincreaseinprioryearreservereleasesonspecialtyreinsurancebusinesslines.Thereinsurancesegmentexperienced favorable reserve development on prior year catastrophe losses including wildfires and other weather-related events, partially offset by reservestrengthening fromTyphoon Jebi in Japan. There was a $13.5 million reduction in prior year reserve releases from$68.4 million in the twelve months endedDecember31,2018.

Policy acquisition, general and administrative expenses.Amortizationof deferred policyacquisitioncosts were$246.0millionfor thetwelvemonthsendedDecember31,2020,equivalentto19.0%ofnetpremiumsearned(2019—$264.9millionor21.1%ofnetpremiumsearned;2018—$260.9millionor20.8%ofnetpremiumsearned).Thedecreaseintheacquisitionratiowasduetochangesinthemixofbusinessandthecededreinsuranceprogram.Theincreaseinpolicyacquisitionexpenseratioin2019comparedwith2018wasduetoanincreaseinprofitcommissiononcertaincontractswithinthereinsurancesegmenttogetherwithreductionsincededover-ridercommissions.

Our general and administrative expenses decreased by $0.9 million from$111.7 million in 2019 to $110.8 million in 2020. Our general and administrativeexpenseratiowas8.6%in2020comparedto8.9%in2019duetocostsavingarisingfromongoinginitiatives. Ourgeneralandadministrativeexpenseratioof8.9%in2019decreasedfrom9.4%in2018duetocostsavingarisingfromourpreviousoperatingeffectivenessandefficiencyinitiative.

Insurance

Ourinsurancesegmentconsistsofpropertyandcasualtyinsurance,marine,aviationandenergyinsurance,andfinancialandprofessionallinesinsurance.Foramoredetaileddescriptionofthissegment,refertoItem4,“BusinessOverview—BusinessSegments—Insurance”andItem18,Note3ofourconsolidatedfinancialstatements,“SegmentReporting.”

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Gross written premiums.ThetablebelowshowsourgrosswrittenpremiumsforeachlineofbusinessforthetwelvemonthsendedDecember31,2020,2019and2018andthepercentagechangeingrosswrittenpremiumsforeachline: Twelve Months EndedLines of Business 2020 2019 2018 ($ in millions) % change ($ in millions) % change ($ in millions)Propertyandcasualtyinsurance $ 942.5 9.4% $ 861.2 (4.7)% $ 903.9Marine,aviationandenergyinsurance 224.4 (25.6)% 301.7 (18.1)% 368.4Financialandprofessionallinesinsurance 875.9 10.3% 794.0 17.0% 678.9

Total $ 2,042.8 4.4% $ 1,956.9 0.3% $ 1,951.2

Theincreaseingrosswrittenpremiumsin2020comparedto2019inpropertyandcasualtyinsurancewasattributabletorateimprovementsacrossourU.S.andU.K. platforms. The increase in gross written premiums in financial and professional lines insurance was largely attributable to rate improvements and newbusiness in Global Professional lines and rate increases in Cyber insurance business. The decrease in gross written premiums in marine, aviation and energyinsurancewaslargelyattributabletoourdecisiontoceaseunderwritinginternationalmarineliabilitybusinessinFebruary2020.

Thedecreaseingrosswrittenpremiumsin2019comparedto2018inpropertyandcasualtyinsurancewaslargelyattributabletoreductionsinourU.K.regionalandU.S.propertybusinesslines, partially offset bygrowthinourU.K.construction, liability, andU.S.excesscasualtybusiness. Thedecreaseingrosswrittenpremiumsinmarine,aviationandenergyinsurancewaslargelyattributabletoreductionsinaviationandLloyd’smarinehullfollowingthedecisiontoexittheselinesinthethirdquarterof2018.ThesereductionswerepartiallyoffsetbygrowthinU.S.inlandmarineandU.S.oceanmarinebusinesslines.TheincreaseingrosswrittenpremiumsinfinancialandprofessionallinesinsurancewaslargelyattributabletogrowthinU.S.professionallines,managementliability,accidentandhealth,andcreditandpoliticalriskbusinesslines.

Ceded written premiums.Totalcededwrittenpremiumsfor2020was$762.0million,adecreaseof$18.1millionfrom2019.Cededwrittenpremiumsdecreasedprimarilyduetoreductionsintheproportionofbusinesscededonmarine,aviationandenergyinsuranceandpropertyandcasualtyinsurance,partiallyoffsetbyanincreaseintheproportionofbusinesscededonfinancialandprofessionallines.

Cededreinsurancefor2019was$780.1million,adecreaseof$272.0millionfrom2018.Cededwrittenpremiumsdecreasedprimarilyduetoreductionsintheproportionofbusinesscededtoourcasualty,financialinstitutionsandpropertyquotashareprograms.

Net premiums earned.Net premiums earned increased by $202.4 million, or 19.5%, in 2020 compared to 2019 largely due to the decision to reduce theproportion of business ceded to reinsurers. Net premiums earned increased by $79.8 million, or 8.3%, in 2019 compared to 2018 due to the impact from thereductionintheproportionofbusinesscededtoourquotasharetreaties.

Losses and loss adjustment expenses.Thelossratioin2020was71.1%comparedto73.4%in2019.Thedecreaseinthelossratioin2020wasprimarilyduetoa$79.2millionincreaseinreservereleases,from$114.4millionstrengtheningin2019to$35.2millionstrengtheningin2020,increaseinnetearnedpremiumsof$202.4million,offsetby$24.5millionincreaseinlargelossesanda$98.7millionincreaseincatastrophelosses.Thelossratioin2019of73.4%increasedfrom67.4%in2018dueprimarilytoa$157.1milliondecreaseinreservereleases,anda$5.0millionincreaseinlargelosses.Thesemovementsmorethanoffsettheimpactfroma$79.8millionincreaseinnetearnedpremiumsanda$34.4milliondecreaseincatastrophelosses.

In2020,theinsurancesegmentexperienced$116.8millionofcatastrophelosses,netofreinsurancerecoverables,dueto$52.5millionfromCOVID-19losses,and$64.3million fromother weather-related events. Largelosses experiencedduring2020included$49.2million, comprisedof $12.9millionof constructionrelatedlosses,$4.0millionofpropertydamagerelatedlosses,$15.3millionofcreditriskrelatedlosses,$14.5millionofaccidentandhealthrelatedlossesand$2.5millionrelatedtocybercrime.

In2019,theinsurancesegmentexperienced$18.1millionofcatastrophelosses,netofreinsurancerecoverables,dueto$2.1millionfromHurricaneDorianand$16.0millionotherweather-relatedevents.Largelossesexperiencedduring2019included$24.6millionofU.S.andotherweather-relatedevents.

In2018,theinsurancesegmentexperienced$52.5millionofcatastrophelosses,netofreinsurancerecoverables,dueto$4.7millionfromU.K.winterstorms,$5.8millionfromHurricaneFlorence,$14.5millionfromwildfiresinCalifornia,$9.6millionfromHurricaneMichael,$1.3millionfromanAlaskanEarthquakeand$16.6 million fromother U.S. andAsianweather-related events. Large losses experienced during2018includeda $6.6 million trade credit loss and$13.0millionoffire-relatedlosses.

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In2020,therewasnetunfavorablereservedevelopmentof$35.2millioncomparedwith$114.4millioninthetwelvemonthsendedDecember31,2019.Thenetunfavorable reserve development was primarily from our property and casualty insurance lines. The reserve strengthening in 2019 was principally from ourpropertyandcasualtyandmarine,aviationandenergylines.Thereservereleasesin2018werepredominantlyfromourpropertyandcasualtyandmarine,aviationandenergylines.Prioryearreservereleasesarefurtherdiscussedunder“ReservesforLossesandLossAdjustmentExpenses”below.

Policy acquisition, general and administrative expenses.Amortizationofdeferredpolicyacquisitioncostswere$219.7millionin2020,equivalentto17.7%ofnetpremiumsearned(2019—$147.8millionor14.2%ofnetpremiumsearned;2018—$110.7millionor11.6%ofnetearnedpremium).Theincreaseintheacquisition expense ratio in 2020compared with 2019was due to reduction in over-rider commissions fromquota share contracts and a change in the mix ofbusiness written. The increase in the acquisition expense ratio in 2019 compared with 2018 was largely due to a change in the mix of business written in theinsurancesegment.

Our general and administrative expenses decreased by $32.6 million to $197.2 million in 2020 from$229.8 million in 2019 (2018 —$239.2 million). Ourgeneralandadministrativeexpenseratiowas15.9%in2020comparedto22.1%in2019duetoourcontinuouseffortsoncostsavingandoperatingeffectivenessinitiatives. Thegeneralandadministrativeexpenseratiowas22.1%in2019comparedto25.0%in2018duetocostsavingarisingfromourpreviousoperatingeffectivenessandefficiencyinitiative.

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Balance Sheet

Total cash and investments

As at December 31, 2020 and December 31, 2019, total cash and investments, including accrued interest receivable were $7.5 billion and $7.8 billion,respectively. Total cash andinvestments were mainly affected bythe transfer of $770.0 million in cashto Enstar as payment for the ADCpremium, offset byadditionalcapitalcontributedbyourparentcompanyHighlandsBermudaHoldco,Ltd.of$268.0million.Ourinvestmentstrategyisfocusedondeliveringstableinvestmentincomeandtotalreturnthroughallmarketcycleswhilemaintainingappropriateportfolioliquidityandcreditqualitytomeettherequirementsofourcustomers,ratingagenciesandregulators.

AsofDecember31,2020,asignificantmajorityoffundsavailableforinvestmentweredeployedinawidelydiversifiedportfolioofhighquality,investmentgradesecurities, includingU.S.government, corporate andU.S. agencymortgage-backedbonds. Wealsoinvest a portionof ourportfolio inother investmentssuchasunratedprivatefixedandfloatingrateinvestmentsandotherspecialtyclasses.Thesesecuritiesgenerallypayhigherrateofinterestorreturnandmayhaveahigherdegreeofcreditordefaultrisk.

BookyieldfortheyearendedDecember31,2020onthefixedincomeportfolio(includingprivateinvestments,shortterminvestmentsandcashwithinthoseportfolios)was2.34%,adecreaseof40basispointsfrom2.74%atDecember31,2019.OurfixedincomeportfoliodurationasatDecember31,2020was2.7yearscomparedto3.2yearsasatDecember31,2019.AsatDecember31,2020,theaveragecreditqualityofourfixedincomeportfoliowas“AA,”with85.0%oftheportfoliobeingrated“A”orhigher.Theaverageratingofourmortgage-backedsecuritieswasAA+.AsatDecember31,2019,theaveragecreditqualityofourfixedincomeportfoliowas“AA-,”with87.9%oftheportfoliobeingrated“A”orhigher.Wherethecreditratingsweresplitbetweenthetwomainratingagencies,S&PandMoody’s,thelowestratingwasused.

AsatDecember31,2020,theCompanyhada1.5%positioninarealestatefundanda3.6%positioninmiddlemarketloans(MML)andcommercialmortgageloans(CML),representingintotal5.1%ofourtotalcashandinvestments,excludingcatastrophebondsandfundsheldbyvariableinterestentities(the“ManagedPortfolio”). Asat December31, 2019, theCompanyhada3.2%positioninU.S. Dollar BBBEmergingMarket Debtanda1.4%positioninareal estate fundrepresentingintotal3.6%ofourManagedPortfolio.

Unrealizedgainsintheavailableforsaleinvestmentportfolio,netoftaxes,were$186.8millionasatDecember31,2020,anincreaseof$102.3millionfromthenet$84.5millionunrealizedgainsasatDecember31,2019.

As at January 1, 2020, we had investments in four entities classified as other investments, equity method: a micro-insurance incubator (“MVI”), BeneAssicurazioni(“Bene”),DigitalRiskResources,LLC(“DigitalRe”)andCropRe.During2020wesoldourinvestmentinBeneandCropRe.AsatDecember31,2020,theCompanyhaspaid$0.5millionofcapitalasanequityinvestmentintheholdingcompanyofamulti-linereinsurer(“Multi-LineReinsurer”),followingtheCompanyhavingpreviously,onDecember23,2019,committed$5.0millionasanequityinvestment.Thestrategyforthemulti-linereinsureristocombineadiversifiedreinsurancebusiness,focusedprimarilyonlong-tailedlinesofpropertyandcasualtybusinessand,potentiallytoalesserextent, lifebusiness,withadiversifiedinvestmentstrategy.

Forfurtherinformationregardingtheseinvestments,refertoItem18,Note4ofourconsolidatedfinancialstatements,“Investments.”

On December 20, 2017, the Company committed to, and during 2018 invested $100.0 million as a limited partner to a real estate fund, classified as otherinvestments.Theinvestmentobjectiveofthefundistoachieveattractiverisk-adjustedreturnsthroughtheacquisitionofincomeproducing,highqualityassetsingateway cities located in the U.S. and Canada in the office, retail, industrial and multifamily sectors of the real estate market. OnMay1, 2018, the Companyreceivedademandforaninitialcapitalcallof$86.2millionandpaidthecapitalcallonMay10,2018.OnSeptember19,2018,theCompanyreceivedademandforthefinal capital call of $13.8millionandpaidthecapital onSeptember28, 2018.Asat December31, 2020thecurrent fair valueofthereal estate fundis$109.4million.

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ThecompositionofourcashandinvestmentsasatDecember31,2020and2019issummarizedbelow: As at December 31, 2020 As at December 31, 2019

Estimated Fair Value

Percentage of Total Cash and

InvestmentsEstimated Fair Value

Percentage of Total Cash and

Investments ($ in millions except for percentages)Fixed Income Securities — Available for SaleU.S.government $ 1,101.2 14.7 % $ 1,413.1 18.1 %U.S.agency 34.3 0.5 39.6 0.5Municipal 67.1 0.9 50.7 0.6Corporate 1,826.2 24.3 1,959.8 25.2Non-U.S.government-backedcorporate 63.4 0.8 86.5 1.1Foreigngovernment 273.1 3.6 328.8 4.2Asset-backed 2.3 — 0.2 —Non-agencycommercialmortgage-backed 7.4 0.1 6.5 0.1Agencymortgage-backed 973.1 13.0 1,073.0 13.9

Total Fixed Income Securities — Available for Sale $ 4,348.1 57.9 % $ 4,958.2 63.7 %Fixed Income Securities — TradingU.S.government 120.5 1.6 % 185.0 2.4 %Municipal 3.5 — 3.2 —Corporate 103.5 1.4 243.2 3.1Highyieldloans 9.8 0.1 — —Foreigngovernment 41.6 0.6 151.2 1.9Asset-backed 539.1 7.2 492.4 6.3Agencymortgage-backedsecurities 37.6 0.5 53.8 0.7

Total Fixed Income Securities — Trading $ 855.6 11.4 % $ 1,128.8 14.4 %Totalotherinvestments,equitymethod 0.9 — 67.9 0.9Totalotherinvestments 109.4 1.5 111.4 1.4Totalcatastrophebonds—trading 18.8 0.3 28.6 0.4Privately-held investments — TradingCommercialmortgageloans 163.6 2.2 156.6 2.0Middlemarketloans 112.1 1.5 111.7 1.4Asset-backedsecurities 18.6 0.2 8.7 0.1Equitysecurities 5.0 0.1 2.7 —

Total privately-held investments — Trading $ 299.3 4.0 % $ 279.7 3.5 %Totalshort-terminvestments—availableforsale 87.8 1.2 117.6 1.5Totalshort-terminvestments—trading 35.4 0.5 79.2 1.0Totalcashandcashequivalents 1,747.3 23.2 1,030.5 13.2

Total Cash and Investments $ 7,502.6 100.0 % $ 7,801.9 100.0 %Netreceivableforsecuritiessold $ 1.4 $ 2.9Accruedinterestreceivable 29.3 39.6

Total Investable Assets $ 7,533.3 $ 7,844.4

__________________Totalotherinvestmentsrepresentsourinvestmentinarealestatefund.ForfurtherinformationrefertoItem18,Note4ourconsolidatedfinancialstatements,

“Investments.”

(1)

(1)

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Ourmortgage-backedportfolioissupportedbyloansdiversifiedacrossanumberofgeographicandeconomicsectors.Thefollowingtablesummarizesthefairvalueofourmortgage-backedsecuritiesbyratingandclassasatDecember31,2020:

AAA AA+ and Below Total ($ in millions)Agency $ — $ 1,010.7 $ 1,010.7Non-agencycommercial — 7.4 7.4Totalmortgage-backedsecurities $ — $ 1,018.1 $ 1,018.1

Theaverageratingofourmortgage-backedportfoliowasAA+.

Sub-prime securities.Wedefinesub-primerelatedinvestmentsasthosesupportedby,orcontaining,sub-primecollateralbasedoncreditworthiness.Wedonotinvestdirectlyinsub-primerelatedsecurities.

AsatDecember31,2020,theCompanyhadinvested$5.0millioninequitysecuritiesinprivately-heldinvestments,aspartoftheCompany’sstrategicassetallocation.WehadnootherinvestmentsinequitysecuritiesasatDecember31,2020.

ThetotalinvestmentreturnfromtradingequityportfoliosforthetwelvemonthsendedDecember31,2020,2019and2018wereasfollows:

For the Twelve Months EndedTrading Equity Portfolio December 31, 2020 December 31, 2019 December 31, 2018 ($ in millions)Dividendincome $ — $ — $ 2.1Realizedinvestmentgains — — 69.5Changeinnetunrealizedgains,grossoftax — — (75.7)Realizedforeignexchangegains — — 4.9Netunrealizedforeignexchangelosses — — (0.6)Totalinvestmentreturnfromthetradingequityportfolio $ — $ — $ 0.2

Valuation of Investments

Fair Value Measurements. OurestimatesoffairvalueforfinancialassetsandliabilitiesarebasedontheframeworkestablishedinthefairvalueaccountingguidanceincludedinASCTopic820,Fair Value Measurements and Disclosures.Foradescriptionoftheframework,refertoItem18,Note6ofourconsolidatedfinancialstatements,“FairValueMeasurements.”

Valuation of Investments, Equity Method. The value of our investments in MVI, Digital Re and Multi-line Reinsurer are based on our share of the capitalposition of the entities which includes income and expenses reported in quarterly management accounts. Each of MVI, Digital Re and Multi-line Reinsurer issubject to annual audit evaluating the financial statements of the entities. Weperiodically reviewthe management accounts of MVI, Digital ReandMulti-lineReinsurerandevaluatethereasonablenessofthevaluationofourinvestment.

Valuation of Other Investments. TheCompany’sotherinvestmentsrepresentourinvestmentinarealestatefund.Adjustmentstothefairvaluearemadebasedonthenetassetvalueoftheinvestment.Thenetvaluationcriteriaestablishedbythemanagerofsuchinvestmentsareestablishedinaccordancewiththegoverningdocumentsandtheassetmanager’svaluationguidelines,whichconsideratwopartapproach:thediscountedcashflowsapproachandtheperformancemultipleapproach,whichusesamultiple/capitalizationratederivedfrommarketmetricsfromcomparablecompaniesorassetstoproduceoperatingperformancemetrics.Alternativevaluationmethodologiesmaybeemployedforinvestmentswithunusualcharacteristics.

Valuation of Privately-held Investments. Privately-heldinvestmentsareinitiallyvaluedatcostortransactionvaluewhichapproximatesfairvalue.Insubsequentmeasurementperiods,thefairvaluesofthesesecuritiesaredeterminedusinginternallydevelopeddiscountedcashflowmodels.Thesemodelsincludeinputsthatarespecifictoeachinvestment.Theinputsusedinthefairvaluemeasurementsincludedividendorinterestratesandappropriatediscountrates.Theselectionofanappropriatediscountrateisjudgmentalandisthemostsignificantunobservableinputusedinthevaluationofthesesecurities.Asignificantincrease(decrease)inthisinputinisolationcouldresultinsignificantlylower(higher)fairvaluemeasurementforotherprivately-heldinvestments.Inordertoassessthereasonablenessof the inputs the Company uses in the discounted cash flow models, the Company maintains an understanding of current market conditions, issuer specificinformationthatmayimpact

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futurecashflowsaswellascollaborationwithindependentvendorsformostsecuritiestoassessthereasonablenessofthediscountratebeingused.Current Expected Credit Losses (“CECL”) / Other-than-temporary Impairment of Investments. Following the Company’s adoption of ASU 2016-13

“Financial Instruments - Credit Losses (Topic 326)”,effectiveJanuary1,2020,creditlossesonavailableforsaledebtsecuritiesaccountingpolicyisapplicable;priortothisdate,thecomparativeperiodspresentedtheother-than-temporaryimpairmentofinvestmentaccountingpolicywhichwasapplicable:

Credit Losses on Available for Sale Debt Securities. A detailed analysis is performed each reporting period end to assess declines in the fair values ofavailableforsaledebtsecurities.Ourcreditlossmodelemploysadiscountedcashflowapproachacrossallassetclasses.Creditlossesareonlycomputedforassetsheldatanunrealizedlossatthebalancesheetdateandwillhaveafairvaluefloor.DefaultprobabilitiesareestimatedforeachratingfromAAAtoCandanalysisisundertakenseparatelyfordifferentassetsclassesandgeographies.Theexpectedcreditlosses,andsubsequentadjustmentstosuchlossesarerecordedwithinnetrealized gains/(losses) and is deducted from the amortized cost basis of the financial asset, with the net carrying value of the financial asset presented on theconsolidatedbalancesheetattheamountexpectedtobecollected.

Following the adoption of these ASUs with effect from January 1, 2020, the Company recognized a reduction in the Company’s available-for-saleinvestmentportfolioby$0.6million,recognizingcurrentexpectedcreditlossesadjustmentof$0.6millionthroughopeningretainedearnings.AsatDecember31,2020werecognizedacreditlossprovisionof$0.2million,realizingagainof$0.4millionwithinthetwelvemonthsendedDecember31,2020.

For further discussion, refer to Item 18, Note 2(c) of our consolidated financial statements, “Basis of Preparation and Significant Accounting Policies —AccountingforInvestments,CashandCashEquivalents.”

Reserves for Losses and Loss Adjustment Expenses

Provisionismadeattheendofeachyearfortheestimatedultimatecostofclaimsincurredbutnotsettledatthebalancesheetdate,includingthecostofIBNRclaims and development of existing reported claims. The estimated cost of claims includes expenses to be incurred in settling claims and a deduction for theexpectedvalueofsalvageandotherrecoveries. Estimatedamountsrecoverablefromreinsurersonunpaidlossesandlossadjustmentexpensesarecalculatedtoarriveatanetclaimsreserve.

Reserves by segment. As at December 31, 2020, we had total net loss and loss adjustment expense reserves of $3,970.1 million (December 31, 2019 —$4,632.0 million). This amount represented our best estimate of the ultimate liability for payment of losses and loss adjustment expenses. Of the total grossreserves for unpaidlossesof $7,165.3millionat thebalancesheet date of December 31, 2020, a total of $3,887.2million, or 54.3%,representedIBNRclaims(December 31, 2019 — $3,682.8 million and 53.0%, respectively). The following tables analyze gross and net loss and loss adjustment expense reserves bybusinesssegmentasatDecember31,2020and2019,respectively: As at December 31, 2020

Business Segment GrossReinsurance Recoverable Net

($ in millions)Reinsurance $ 3,150.6 $ (1,054.9) $ 2,095.7Insurance 4,014.7 (2,140.3) 1,874.4Totallossesandlossexpensereserves $ 7,165.3 $ (3,195.2) $ 3,970.1

At December 31, 2019

Business Segment GrossReinsurance Recoverable Net

($ in millions)Reinsurance $ 3,152.9 $ (547.0) $ 2,605.9Insurance 3,798.9 (1,772.8) 2,026.1Totallossesandlossexpensereserves $ 6,951.8 $ (2,319.8) $ 4,632.0

Theincreaseinreinsurancerecoverables in2020comparedwith2019wasduepredominantlytotherecognitionofanadditional $770.0millionreinsurancerecoverable upon entering into an adverse development cover reinsurance agreement with a subsidiary of Enstar, pursuant to which Enstar’s subsidiary willreinsurelossesincurredonorpriortoDecember31,2019.

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Enstar’ssubsidiarywillprovide$770.0millionofcoverinexcessof$3.805billionretentionuptoanaggregateof$4.575billion,andanadditional$250.0millionofcoverinexcessabove$4.815billion,upto$5.065billion.

ThegrossreservesmaybefurtheranalyzedbetweenoutstandingclaimsandIBNRasatDecember31,2020and2019asfollows: As at December 31, 2020

GrossOutstandings

GrossIBNR

GrossReserve % IBNR

($ in millions, except for percentages)Reinsurance $ 1,541.3 $ 1,609.3 $ 3,150.6 51.1 %Insurance 1,736.8 2,277.9 4,014.7 56.7 %Totallossesandlossexpensereserves $ 3,278.1 $ 3,887.2 $ 7,165.3 54.3 %

As at December 31, 2019

GrossOutstandings

GrossIBNR

GrossReserve % IBNR

($ in millions, except for percentages)Reinsurance $ 1,535.8 $ 1,617.1 $ 3,152.9 51.3 %Insurance 1,733.2 2,065.7 3,798.9 54.4 %Totallossesandlossexpensereserves $ 3,269.0 $ 3,682.8 $ 6,951.8 53.0 %

Prior year loss reserves.ForthetwelvemonthsendedDecember31,2020,overallourestimateofultimatenetclaimstobepaidinrespectofprioraccidentyearsremainedbroadlyunchanged,decreasing$0.9million.Ananalysisofthisoverallnetincrease/(decrease)bybusinesssegmentisasfollowsforeachofthetwelvemonthsendedDecember31,2020,2019and2018: For the Twelve Months EndedBusiness Segment December 31, 2020 December 31, 2019 December 31, 2018 ($ in millions)Reinsurance $ 36.1 $ 54.9 $ 68.4Insurance (35.2) (114.4) 42.7Totallossesandlossexpensereserveschanges $ 0.9 $ (59.5) $ 111.1

For the twelve months ended December 31, 2020.Theanalysisofthedevelopmentbyeachsegmentisasfollows:

Reinsurance.Netreservereleasesof$36.1millionin2020weremainlyduetoreleasesoncasualtyreinsurance,propertycatastrophereinsuranceandspecialtyreinsurance,partiallyoffsetbystrengtheningonotherpropertyreinsurancelines.

Insurance.Netunfavorablereservedevelopmentof$35.2millionin2020wasprimarilyfromourpropertyandcasualtylinesandfinancial andprofessionallines,partiallyoffsetbynetfavorablereservedevelopmentonmarine,aviationandenergylines.

For the twelve months ended December 31, 2019.Theanalysisofthedevelopmentbyeachsegmentisasfollows:

Reinsurance.Netreservereleasesof$54.9millionin2019weremainlyasaresultoffavorabledevelopmentinpropertycatastrophereinsurance,otherpropertyreinsurance and specialty reinsurance lines. The property catastrophe and other property reinsurance business lines reported favorable development due toreductions in estimated losses from 2018 catastrophes. The specialty reinsurance business lines reported net reserve releases due primarily to favorabledevelopmentonmarinereinsurancelines.ThecasualtyreinsurancebusinesslinesreportednetreservestrengtheningdueprimarilytounfavorabledevelopmentonU.S.casualtylines.

Insurance.Net reserve strengthening of $114.4 million in 2019 were mainly as a result of unfavorable development in property and casualty and marine,aviation and energy lines partially offset by modest reserves releases for financial and professional lines. The property and casualty business lines reportedunfavorabledevelopmentdueprimarilytounfavorabledevelopmentonU.S.primarycasualtylines.Themarine,aviationandenergybusinesslinesreportednetreservestrengtheningdueprimarilytounfavorabledevelopmentoninternationalmarineandenergyliabilityproducts,whichwereexitedinFebruary2020.

Wedidnotmakeanysignificantchangesinmethodologiesusedinourreservingprocess.

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Critical Accounting Policies

Ourconsolidatedfinancialstatementscontaincertainamountsthatareinherentlysubjectiveinnatureandrequiremanagementtomakeassumptionsandbestestimatestodeterminethereportedvalues.Webelievethatthefollowingcriticalaccountingpoliciesaffectthemoresignificantestimatesusedinthepreparationofourconsolidatedfinancialstatements.AstatementofallthesignificantaccountingpoliciesweusetoprepareourfinancialstatementsisincludedintheNotestothe consolidated financial statements. If factors such as those described in Item3D, “Risk Factors” cause actual events to differ fromthe assumptions used inapplyingtheaccountingpoliciesandcalculatingfinancialresults,therecouldbeamaterialadverseeffectonouroperatingresults,financialconditionandliquidity.

Written Premiums

Written premiums comprise the estimated premiums on contracts of insurance and reinsurance entered into in the reporting period, except in the case ofproportionalreinsurancecontracts,wherewrittenpremiumsrelateonlytoourestimatedproportionalshareofpremiumsdueoncontractsenteredintobythecedingcompanypriortotheendofthereportingperiod.

Allpremiumestimatesarereviewedregularly,comparingactualreportedpremiumstoexpectedultimatepremiumsalongwithareviewofthecollectabilityofpremiums receivable. Based on management’s review, the appropriateness of the premium estimates is evaluated, and any adjustments to these estimates arerecorded in the periods in which they become known. Adjustments to original premium estimates could be material and these adjustments may directly andsignificantlyimpactearningsintheperiodtheyaredeterminedbecausethesubjectpremiummaybefullyorsubstantiallyearned.

Werefertopremiumsreceivablewhicharenotfixedattheinceptionofthecontractasadjustmentpremiums.Theproportionofadjustmentpremiumsincludedinthepremiumestimatesvariesbetweenbusinesslineswiththelargestadjustmentpremiumsassociatedwithpropertyandcasualtyreinsurancebusinessandthesmallestwithpropertyandliabilityinsurancelines.

Adjustmentpremiumsaremostsignificantinrelationtoreinsurancecontracts.Differentconsiderationsapplytonon-proportionalandproportionaltreatiesasfollows:

Non-proportional treaties.Alargenumberofthereinsurancecontractswewritearewrittenonanon-proportionalorexcessoflosstreatybasis.Astheultimatelevelofbusinesswrittenbyeachcedantcanonlybeestimatedatthetimethereinsuranceisplaced,thereinsurancecontractsgenerallystipulateaminimumanddepositpremiumpayableunderthecontractwithanadjustablepremiumdeterminedbyvariablessuchasthenumberofcontractscoveredbythereinsurance,thetotal premiumreceivedbythecedantandthenatureoftheexposuresassumed.Minimumanddeposit premiumsgenerallycoverthemajorityofpremiumsdueundersuchtreatyreinsurancecontractsandtheadjustableportionofthepremiumisusuallyasmall portionofthetotal premiumreceivable. Forexcessoflosscontracts, the minimum and deposit premium, as defined in the contract, is generally considered to be the best estimate of the contract’s written premium atinception.Accordingly,thisistheamountwegenerallyrecordaswrittenpremiumintheperiodtheunderlyingrisksincept.

Duringthelifeofacontract,notificationsfromcedantsandbrokersmayaffecttheestimateofultimatepremiumandresultineitherincreasesorreductionsinreported revenue. Changes in estimated adjustable premiums do not generally have a significant impact on short-term liquidity as the payment of adjustmentpremiumsgenerallyoccursaftertheexpirationofacontract.

Manynon-proportional treaties alsoincludeaprovisionforthepaymenttousbythecedantofreinstatementpremiumsbasedonlossexperienceundersuchcontracts. Reinstatement premiums are the premiums charged for the restoration of the reinsurance limit of an excess of loss contract to its full amount afterpaymentbythereinsureroflossesasaresultofanoccurrence.Thesepremiumsrelatetothefuturecoverageobtainedduringtheremainderoftheinitialpolicytermandareincludedinrevenueinthesameperiodasthecorrespondinglosses.

Proportional treaties (“treaty pro rata”).Estimatesofpremiumsassumedundertreatyproratareinsurancecontractsarerecordedintheperiodinwhichtheunderlying risks are expected to incept and are based on information provided by brokers and ceding companies and estimates of the underlying economicconditionsatthetimetheriskisunderwritten.Weestimatepremiumsreceivableinitiallyandupdateourpremiumestimatesregularlythroughoutthecontracttermbasedontreatystatementsreceivedfromthecedingcompany.

Thereportedgrosswrittenpremiumsfortreatyproratabusinessincludeestimatesofpremiumsduetousbutnotyetreportedbythecedantbecauseoftimedelaysbetweencontractsbeingwrittenbyourcedantsandtheirsubmissionoftreatystatementstous.Thisadditionalpremiumisnormallydescribedaspipelinepremium. Treaty statements disclose information on the underlying contracts of insurance written by our cedants and are generally submitted on a monthly orquarterlybasis,from30to90daysinarrears.Inordertoreportallrisksinceptingpriortoaperiodend,weestimatethepremiumswrittenbetweenthelast

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submittedtreatystatementandtheperiodend.Treatyproratapremiumsarewrittenpredominantlyinourotherproperty,specialtyandcasualtyreinsurancelinesofbusiness.

Propertytreatyproratacontributedsignificantlytoourreinsurancesegmentwherewewrote$285.1millioningrosswrittenpremiumin2020(2019—$251.4million),or17.2%ofthegrosswrittenpremiumsinourreinsurancesegment,ofwhich$5.0millionwasestimated(2019—$36.9million)and$280.1millionwasreportedbythecedants(2019—$214.5million).Excludingtheimpactofcosts,suchasreinsurancepremiumsandoperatingexpenses,weestimatethattheimpactofa$1.0millionincrease/decreaseinourestimatedgrosswrittenpremiumsinourpropertytreatyproratabusinesswouldincrease/decreasenetincomebeforetaxbyapproximately$0.1millionfortheyearendedDecember31,2020(2019—$0.1millionincrease/decrease).

Themostlikelydriversofchangeinourpremiumestimatesindecreasingorderofmagnitudeare:

• changesinrenewalrateorrateofnewbusinessacceptancesbycedantinsurancecompaniesleadingtolowerorgreatervolumesofcededpremiumsthanourestimate,whichcouldresultfromchangesintherelevantprimarymarketthatcouldaffectmorethanoneofourcedantsorcouldbeaconsequenceofchangesinmarketingstrategyorriskappetitebyaparticularcedant;

• changesintheratesbeingchargedbycedants;and

• differencesbetweenthepatternofinceptiondatesassumedinourestimateandtheactualpatternofinceptiondates.

Weanticipatethatultimatepremiumsmightreasonablybeexpectedtovarybyupto5%asaresultofvariationsinoneormoreoftheassumptionsdescribedabove,althoughlargervariationsarepossible.Basedongrosswrittenpremiumsof$285.1million(2019—$251.4million)inourpropertyreinsurancetreatyprorataaccountasatDecember31,2020,avariationof5%couldincreaseorreducenetincomebeforetaxbyapproximately$Nil(2019—$0.1million).

Earned premiums.Premiumsarerecognizedasearnedoverthepolicyexposureperiods.Thepremiumrelatedtotheunexpiredportionofeachpolicyattheendofthereportingperiodisincludedinthebalancesheetasunearnedpremiums.

Reserving Approach

Weare required by U.S. GAAP to establish loss reserves for the estimated unpaid portion of the ultimate liability for losses and loss expenses (“ultimatelosses”)underthetermsofourpoliciesandagreementswithourinsuredandreinsuredcustomers.Ourlossreservescomprisethefollowingcomponents:

• thecostofclaimsreportedtousbutnotyetpaidknownascasereserves(“casereserves”);

• ReservestocovertheanticipatedcostofIBNRclaims.Withinthis,wealsoincludethepotentialdevelopmentofreportedclaims;and

• the expenses associated with settling claims, including legal and other fees and the general expenses of administering the claims adjustment process,knownasthelossadjustmentexpenses(“LAE”).

Priortotheselectionofthereservestobeincludedinourfinancialstatements,ouractuarialteamemploysanumberoftechniquestodeterminetheactuarialcentralestimatewhichispresentedtotheGroupLossReserveCommittee.TheCommitteereviewsandevaluatestheactuarialcentralestimateandprovidesinputtomanagementforitsdeterminationofthemanagementbestestimate.

Case Reserves. For reported claims, reserves are established ona case-by-case basis within the parameters of coverage providedin the insurance policy orreinsuranceagreement.Themethodofestablishingcasereservesforreportedclaimsdiffersamongouroperations.Withrespecttoourinsuranceoperations,weareadvised of potential insured losses and our claims handlers’ record reserves for the estimated amount of the expected indemnity settlement, loss adjustmentexpensesandcostofdefensewhereappropriate.Thereserveestimatereflectsthejudgmentoftheclaimspersonnelandisbasedonclaiminformationobtainedtodate, general reserving practices, the experience and knowledge of the claims personnel regarding the nature of the specific claim and where appropriate andavailable,advicefromlegalcounsel,lossadjustersandotherclaimsexperts.

Withrespecttoourreinsuranceclaimsoperations,claimshandlerssetcasereservesforreportedclaimsgenerallybasedontheclaimsreportsreceivedfromourcedingcompaniesandtakeintoconsiderationourcedants’ownreserverecommendationsandourpriorlossexperiencewiththecedant.Additionalcasereserves(“ACR”),inadditiontothecedants’ownrecommendedreserves,maybeestablishedbyustoreflectourestimatedultimatecostofaloss.ACRsaregenerallytheresultofeithera

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claims handler’s ownexperience and knowledge of handling similar claims, general reserving practices or the result of reserve recommendations following anauditofcedants’reserves.

Casereservesarebasedonasubjectivejudgmentoffactsandcircumstancesandareestablishedforthepurposesofinternalreservingonly.Accordingly,theydonotrepresentacommitmenttoanycourseofconductoradmissionofliabilityonourbehalfinrelationtoanyspecificclaim.

IBNR Reserves.TheneedforIBNRreservesarisesfromtimelagsbetweenwhenalossoccursandwhenitisactuallyreportedandsettled.Bydefinition,wedonot havespecific informationonIBNRclaimssotheyneedto beestimatedbyactuarial methodologies. IBNRreserves are therefore generally calculated at anaggregatelevelandcannotgenerallybeidentifiedasreservesforaparticularlossorcontract.WecalculateIBNRreservesbyclassofbusinesswithineachlineofbusiness.Whereappropriate,analysesmaybeconductedonsub-setsofaclassofbusiness.IBNRreservesarecalculatedbyprojectingourultimatelossesoneachclassofbusinessandsubtractingpaidlossesandcasereserves.IBNRreservesalsocovertheanticipatedcostofclaimsincurredbutnotreported,withinthiswealsoincludeanypotentialdevelopmentofreportedclaims.Overrecentyears,wehavebeguntoplacegreaterrelianceonouractualactuarialexperienceforourlong-tail lines of business that we have written since our inception in 2002. We believe that our earliest accident years are nowcapable of providing us withmeaningfulactuarialindications.EstimatesandjudgmentsfornewinsuranceandreinsurancelinesofbusinessaremoredifficulttomakethanthosemadeformorematurelinesofbusinessbecausewehavemorelimitedhistoricalinformationthroughDecember31,2020.

Sources of Information.Claimsinformationreceivedtypicallyincludesthelossdate,detailsoftheclaim,therecommendedreserveandreportsfromthelossadjusters dealing with the claim. In respect of pro rata treaties and any business written through managing general agents, we receive regular statements(bordereaux)whichprovidepaidandoutstandingclaimsinformation,oftenwithlargelossesseparatelyidentified.Followingwidelyreportedlossevents,suchascatastrophes, weadoptaproactiveapproachtoestablishourlikelyexposuretoclaimsbyreviewingpolicylistingsandcontactingbrokersandpolicyholders asappropriate.

Actuarial Methodologies.Themainprojectionmethodologiesthatareusedbyouractuariesareasfollows:

• Initial expected loss ratio (“IELR”) method:Thismethodcalculatesanestimateofultimatelossesbyapplyinganestimatedlossratiotoanestimateofultimate earned premium for each accident year. The estimated loss ratio may be based on pricing information and/or industry data and/or historicalclaimsexperiencerevaluedtotheyearunderreview.

• Bornhuetter-Ferguson (“BF”) method:TheBFmethodusesasastartingpointanassumedIELRandblendsinthelossratio,whichisimpliedbytheclaimsexperiencetodateusingbenchmarklossdevelopmentpatternsonpaidclaimsdata(“PaidBF”)orreportedclaimsdata(“ReportedBF”).Althoughthemethodtendstoprovidelessvolatileindicationsatearlystagesofdevelopmentandreflectschangesintheexternalenvironment, it canbeslowtoreact to emergingloss development andcan, if theIELRprovestobeinaccurate, produceloss estimates whichtakelonger toconvergewiththefinalsettlementvalueofloss.

• Loss development (“Chain Ladder”) method:Thismethodusesactuallossdataandthehistoricaldevelopmentprofilesonolderaccidentyearstoprojectmorerecent,lessdevelopedyearstotheirultimateposition.

• Exposure-based method:Thismethodistypicallyusedforspecificlargecatastrophiceventssuchasamajorhurricane.Allexposureisidentifiedandweworkwithknownmarketinformationandinformationfromourcedantstodetermineapercentageoftheexposuretobetakenastheultimateloss.

Inadditiontothesemethodologies,ouractuariesmayuseotherapproachesdependinguponthecharacteristicsoftheclassofbusinessandavailabledata.

Ingeneralterms,theIELRmethodismostappropriateforclassesofbusinessand/oraccidentyearswheretheactualpaidorreportedlossexperienceisnotyetmatureenoughtomodifyourinitialexpectationsoftheultimatelossratios.Typicalexampleswouldberecentaccidentyearsforclassesofbusinessincasualtyreinsurance.TheBFmethodisgenerallyappropriatewheretherearefewreportedclaimsandarelativelylessstablepatternofreportedlosses.Typicalexampleswouldbeourtreatyriskexcessclassofbusinessinourreinsurancesegmentandmarinehullclassofbusinessinourinsurancesegment.TheChainLaddermethodis appropriate when there are relatively stable patterns of loss emergence and a relatively large number of reported claims. Typical examples are the U.K.commercialpropertyandU.K.commercialliabilityclassesofbusinessinourinternationalinsurancebusiness.

Reserving Procedures and Process.OuractuariescalculatetheIELR,BFandChainLadderand,ifappropriate,othermethodsforeachclassofbusinessandeachaccidentyear.Theythencalculateasinglepointactuarialcentralestimate(“ultimate”)foreachclassofbusinessandprovideastochasticdistributionaroundthemeanforeachlineofbusiness.The

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actuarialmethodologiesinvolvesignificantsubjectivejudgmentsreflectingmanyfactors,includingbutnotlimitedto,changesinlegislativeconditions,changesinjudicial interpretation of legal liability policy coverages and inflation. Our actuaries collaborate with our underwriting, claims, legal and finance teams inidentifyingfactorswhichareincorporatedintheirrangeofultimatesinwhichmanagement’sbestestimateismostlikelytofall.

Therearenodifferencesbetweenouryear-endandourquarterlyinternalreservingproceduresandprocessesbecauseouractuariesperformthebasicprojectionsandanalysesdescribedaboveforeachclassofbusinessquarterly.

Selection of Reported Gross Reserves.TheReserveCommittee,reviewsandevaluatestheactuarialcentralestimateandprovidesinputtomanagementforitsdetermination of management best estimate of reserves for each line of business. Management selects the “management best estimate” by considering all theinformationprovidedtothemandtherisksanduncertaintiesassociatedwiththeactuarialmeanbestestimate.Managementhastodateselecteditsbestestimateabovethatoftheactuarialcentralestimate.Themanagement’sbestestimateprovidesthebasisformanagement’srecommendationtotheAuditCommitteeandtheBoardregardingthereserveamountsandrelateddisclosurestoberecordedinourfinancialstatements.

ThereisoneReserveCommittee,thatmakesfinalreservingrecommendations.TheReserveCommitteecurrentlyconsistsoftheGroupChiefFinancialOfficer(thechairperson),thePresidentandChiefUnderwritingOfficerofAspenRe,thePresidentandChiefUnderwritingOfficerofAspenInsurance,theGroupCEOandtheGroupChiefActuary.

EachclassofbusinessisreviewedindetailbymanagementthroughitsReserveCommitteeatleastonceayear.Thetimingofsuchreviewsvariesthroughoutthe year. Additionally, wereviewthe emergence of actual losses relative to expectations everyfiscal quarter for all classes of business. If warrantedfromthisanalysis,wemayacceleratethetimingofourdetailedactuarialreviews.

Uncertainties.Whilethemanagementselectedreservesmakeareasonableprovisionforunpaidlossandlossadjustmentexpenseobligations,wenotethattheprocessofestimatingrequiredreserves,byitsverynature,involvesuncertaintyandthereforetheultimateclaimsmayfalloutsidetheactuarialrange.Thelevelofuncertaintycanbeinfluencedbysuchfactorsastheexistenceofcoveragewithlongdurationreportingpatternsandchangesinclaimshandlingpractices,aswellastheotherfactorsdescribedabove.

Givenmanyofthecoveragesunderwritteninvolveclaimsthatmaynotbeultimatelysettledformanyyearsaftertheyareincurred,subjectivejudgmentsastothe ultimate exposure to losses are an integral and necessary component of the loss reserving process. We review our reserves regularly, using a variety ofstatistical and actuarial techniques to analyze current claims costs, frequency and severity data, and prevailing economic, social and legal factors. Reservesestablishedinpriorperiodsareadjustedasclaimsexperiencedevelopsandnewinformationbecomesavailable.

Estimates of IBNRare generally subject to a greater degree of uncertainty than estimates of the cost of settling claims already notified to us, where moreinformationabouttheclaimeventisgenerallyavailable.IBNRclaimsoftenmaynotbeapparenttotheinsureduntilmanyyearsaftertheeventgivingrisetotheclaims has happened. Classes of business where the IBNR proportion of the total reserve is high, such as casualty insurance, will typically display greatervariationsbetweeninitialestimatesandfinaloutcomesbecauseofthegreaterdegreeofdifficultyofestimatingthesereserves.

Classesofbusinesswhereclaimsaretypicallyreportedrelativelyquicklyaftertheclaimeventtendtodisplaylowerlevelsofvolatilitybetweeninitialestimatesandfinaloutcomes.Reinsuranceclaimsaresubjecttoalongertimelagbothintheirreportingandintheirtimetofinalsettlement.Thetimelagisafactorwhichisincluded in the projections to ultimate claims within the actuarial analyses and helps to explain why in general a higher proportion of the initial reinsurancereservesarerepresentedbyIBNRthanforinsurancereservesforbusinessinthesameclass.DelaysinreceivinginformationfromcedantsareanexpectedpartofnormalbusinessoperationsandareincludedwithinthestatisticalestimateofIBNRtotheextentthatcurrentlevelsofbacklogareconsistentwithhistoricaldata.Currently,therearenoprocessingbacklogswhichwouldmateriallyaffectourfinancialstatements.

Allowanceismade,however,forchangesoruncertaintieswhichmaycreatedistortionsintheunderlyingstatisticsorwhichmightcausethecostofunsettledclaimstoincreaseorreducewhencomparedwiththecostofpreviouslysettledclaims,including:

• changesinourprocesseswhichmightaccelerateorslowdownthedevelopmentand/orrecordingofpaidorincurredclaims;

• changesinthelegalenvironment(includingchallengestotortreform);

• theeffectsofinflation;

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• changesinthemixofbusiness;

• theimpactoflargelosses;and

• changesinourcedants’reservingmethodologies.

Thesefactorsareincorporatedintherecommendedreserverangefromwhichmanagementselectsitsbestpointestimate.Wetakeallreasonablestepstoensurethat we utilize all appropriate information and actuarial techniques in establishing our IBNR reserves. However, given the uncertainty in establishing claimsliabilities, it islikelythatthefinaloutcomewillprovetobedifferentfromtheoriginalprovisionestablishedatthebalancesheetdate.Changestoourpreviousestimatesofpriorperiodlossreservesimpactthereportedcalendaryearunderwritingresultsbyworseningourreportedresultsiftheprioryearreservesprovetobedeficientorimprovingourreportedresultsiftheprioryearreservesprovetoberedundant.AsatDecember31,2020,a5%changeinthegrossreserveforIBNRlosseswouldhaveequatedtoachangeofapproximately$194.4millioninlossreserveswhichwouldrepresent617.1%oflossbeforeincometaxforthetwelvemonthsendedDecember31,2020.AsatDecember31,2019,a5%changeinthegrossreserveforIBNRlosseswouldhaveequatedtoachangeofapproximately$184.1millioninlossreserveswhichwouldrepresent84.1%ofincomebeforeincometaxforthetwelvemonthsendedDecember31,2019.A5%changeinournetlossreservesequatesto$198.5millionandrepresents6.6%ofshareholders’equityasatDecember31,2020.

Therearespecificareasofourselectedreserveswhichhaveadditionaluncertaintyassociatedwiththem.RefertoItem3D,“RiskFactors—InsuranceRisks—Our financial condition and operating results maybe adversely affected if actual claims exceed our loss reserves” for a discussion of the specific areas of ourselected reserves which have additional uncertainty. In each case, management believes they have selected an appropriate best estimate based on currentinformationandcurrentanalyses.

Loss Reserving Sensitivity Analysis.Themostsignificantkeyassumptionsidentifiedinthereservingprocessarethat(i)thehistoriclossdevelopmentandtrendexperienceisassumedtobeindicativeoffuturelossdevelopmentandtrends,(ii)theinformationdevelopedfrominternalandindependentexternalsourcescanbeused to develop meaningful estimates of the initial expected ultimate loss ratios, and (iii) no significant losses or types of losses will emerge that are notrepresentedineithertheinitialexpectedlossratiosorthehistoricaldevelopmentpatterns.

Webelievethatthereispotentiallysignificantriskinestimatinglossreservesforlong-taillinesofbusinessandforimmatureaccidentyearsthatmaynotbeadequatelycapturedthroughtraditionalactuarialprojectionmethodologies.Asdiscussedabove,thesemethodologiesusuallyrelyheavilyonprojectionsofprioryeartrendsintothefuture.Inselectingourbestestimateoffutureliabilities,weconsiderboththeresultsofactuarialpointestimatesoflossreservesinadditiontothestochasticdistributionofreserves.Indeterminingtheappropriatebestestimate,wereview(i)thepositionofoverallreserveswithintheactuarialdistribution,(ii) the result of bottom up analysis by accident year reflecting the impact of parameter uncertainty in actuarial calculations, and (iii) specific qualitativeinformationoneventsthatmayhaveaneffectonfutureclaimsdevelopmentbutwhichmaynothavebeenadequatelyreflectedinactuarialbestestimates,suchasthepotentialforoutstandinglitigationorclaimspracticesofcedantstohaveanadverseimpact.

Effect if Actual Results Differ From Assumptions.Given the risks and uncertainties associated with the process for estimating reserves for losses and lossexpenses, management has performed an evaluation of the potential variability in loss reserves and the impact this variability may have on reported results,financialconditionandliquidity.Becauseoftheinherentuncertaintiesdiscussedabove,wehavedevelopedareservingphilosophywhichattemptstoincorporateprudentassumptionsandestimates,andwehavegenerallyexperiencedfavorablenetdevelopmentonprioryearreservesinthelastseveralyears.However,thereisnoassurancethatthiswilloccurinfutureperiods.

Management’sbestestimateofthenetreserveforlossesandlossexpensesasatDecember31,2020was$3,970.1million.ThefollowingtablesshowtheeffectonestimatednetreservesforlossesandlossexpensesasatDecember31,2020ofachangeintwoofthemostcriticalassumptionsinestablishingreserves:(i)lossemergencepatterns,acceleratedordeceleratedbythreeandsixmonths;and(ii)expectedlossratiosvariedbyplusorminusfiveandtenpercent.Acceleratedlossemergencepatternsindicatesahigherdevelopmentpercentageoflosses,thereforerequiringlowerIBNRthanpreviouslyexpectedandhenceresultinginalowerultimate.

Management believes that these scenarios present a reasonable range of variability around the booked reserves using standard actuarial techniques. Lossreservesmayvarybeyondthesescenariosinperiodsofheightenedorreducedclaimactivity.Thereservesresultingfromthechangesintheassumptionsarenotadditive and should be considered separately. The following tables vary the assumptions employed therein independently. In addition, the tables belowdo notadjustanyparametersotherthantheonesdescribedabove.

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Net reserve for losses and loss expenses as at December 31, 2020 — Sensitivity to loss emergence patternsChange in assumption Reserve for losses and loss expenses

($ in millions)Sixmonthacceleration $ 3,699.6Threemonthacceleration $ 3,834.8Nochange(selected) 3,970.1Threemonthdeceleration $ 4,105.4Sixmonthdeceleration $ 4,240.6

Net reserve for losses and loss expenses as at December 31, 2020 — Sensitivity to expected loss ratios

Change in assumption Reserve for losses and loss expenses($ in millions)

10%favorable $ 3,738.95%favorable $ 3,848.6Nochange(selected) 3,970.15%unfavorable $ 4,122.510%unfavorable $ 4,303.6

Themostsignificantvarianceintheabovescenarios(i.e.,a10%unfavorablemovementinexpectedlossratios)wouldhavetheeffectofincreasinglossesandlossexpensesby$333.5million.Thereserveforunallocatedlossadjustmentexpenses,includedwithintheabovesensitivityanalysis,canalsovaryduetochangesinyieldassumptionswherea0.1%decreasecouldhavetheeffectofincreasinglossandlossexpensesbyanestimated$20million.

Managementbelievesthatthereserveforlossesandlossexpensesaresufficienttocoverexpectedclaimsincurredbeforethereportingdateonthebasisofthemethodologiesandjudgmentsusedtosupportitsestimates.However,therecanbenoassurancethatactualpaymentswillnotvarysignificantlyfromtotalreserves.Thereserveforlossesandlossexpensesandthemethodologyofestimatingsuchreserveareregularlyreviewedandupdatedasnewinformationbecomesknown.Anyresultingadjustmentsarereflectedinincomeintheperiodinwhichtheybecomeknown.

Valuation of Investments Measured Using Significant Unobservable Inputs

TheCompany’sestimatesoffairvalueforfinancialassetsandliabilitiesarebasedontheframeworkestablishedinthefairvalueaccountingguidanceincludedin ASCTopic 820, “Fair Value Measurements andDisclosures.” The framework prioritizes the inputs, which refer broadly to assumptions market participantswoulduseinpricinganassetorliability.

TheCompanyconsiderspricesforactivelytradedsecuritiestobederivedbasedonquotedpricesinanactivemarketforidenticalassets.

TheCompanyconsiderspricesforothersecuritiesthatmaynotbeasactivelytradedwhicharepricedviapricingservices,vendorsandbroker-dealers,orwithreferencetointerestratesandyieldcurves,tobederivedbasedoninputsthatareobservablefortheasset,eitherdirectlyorindirectly,

TheCompanyconsiderssecurities,otherfinancialinstruments,privately-heldinvestmentsandderivativeinsurancecontractssubjecttofairvaluemeasurementwhosevaluationisderivedbyinternalvaluationmodelstobebasedlargelyonunobservableinputs.UnobservableinputsareassumptionsusedbytheCompanyusingthebestavailableinformationatthetimeofmakingthesevaluationassumptions.Level3financialinstrumentshavetheleastuseofobservablemarketinputsusedtodeterminefairvalue.AsatDecember31,2020,theCompanyclassifiedprivately-heldinvestmentsof$299.3millionasLevel3asaresultofsignificantunobservableinputsusedtodeterminefairvalue.

Privately-heldinvestmentsareinitiallyvaluedatcostortransactionvaluewhichapproximatesfairvalue.Insubsequentmeasurementperiods,thefairvaluesofthese securities are determined usinginternally developeddiscounted cash flowmodels. These models include inputs that are specific to each investment. Theinputs used in the fair value measurements include dividend or interest rates and appropriate discount rates. The selection of an appropriate discount rate isjudgmentalandisthemostsignificantunobservableinputusedinthevaluationofthesesecurities.Asignificantincrease(decrease)inthisinputinisolationcouldresultinsignificantlylower(higher)fairvaluemeasurementforprivately-heldinvestments.InordertoassessthereasonablenessoftheinputstheCompanyusesinthediscountedcashflowmodels,theCompanymaintainsan

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understandingofcurrentmarketconditions,issuerspecificinformationthatmayimpactfuturecashflowsaswellascollaborationwithindependentvendorsformostsecuritiestoassessthereasonablenessofthediscountratebeingused.

TheCompany’s other investments represent our investment in a real estate fund. Adjustments to thefair valueare madebasedonthenet asset valueof theinvestment.Thenetvaluationcriteriaestablishedbythemanagerofsuchinvestmentsareestablishedinaccordancewiththegoverningdocumentsandtheassetmanager’s valuationguidelines, whichconsideratwopart approach: thediscountedcashflowsapproachandtheperformancemultiple approach, whichusesamultiple/capitalizationrate derivedfrommarket metrics fromcomparable companies or assets to produceoperatingperformancemetrics. Alternativevaluationmethodologiesmaybeemployedforinvestmentswithunusualcharacteristics.

SeealsoQuantitative andQualitative disclosures about Market Riskin Item11of this report for further details oninterest rate andcredit spreadrisk andasensitivityanalysisofinterestrateonthevaluationoftheCompany’sinvestment.

B. Liquidity and Capital Resources

Liquidity

Liquidityisameasureofacompany’sabilitytogeneratecashflowssufficienttomeetshort-termandlong-termcashrequirementsofitsbusinessoperations.Management monitors the liquidity of Aspen Holdings and of each of its Operating Subsidiaries and arranges credit facilities to enhance short-term liquidityresourcesonastand-bybasis.Asaholdingcompany,AspenHoldingsreliesondividendsandotherdistributionsfromitsOperatingSubsidiariestoprovidecashflow to meet ongoing cash requirements, including any future debt service payments and other expenses, and to pay dividends, if any, to our preference andordinaryshareholders.

AsatDecember31,2020,AspenHoldingsheld$91.9million(December31,2019—$117.6million)ofcash,cashequivalentsandinvestments.Managementconsiders the current cash and cash equivalents, together with dividends declared or expected to be declared by subsidiary companies and our credit facilities,sufficienttoappropriatelysatisfytheliquidityrequirementsofAspenHoldings.AspenHoldings’liquiditydependsondividends,capitaldistributionsandinterestpaymentsfromourOperatingSubsidiaries.AspenHoldingsalsohasrecoursetothecreditfacilitydescribedunder“LetterofCreditFacilities”below.

TheabilityofourOperatingSubsidiariestopaydividendsorotherdistributionsissubjecttothelawsandregulationsapplicabletoeachjurisdiction,aswellasthe Operating Subsidiaries’ need to maintain capital requirements adequate to maintain their insurance and reinsurance operations and their financial strengthratingsissuedbyindependentratingagencies.WedonotexpecttosuffertaxonforeignearningssinceoursignificantsourceofearningsoutsideofBermudaistheU.K.andnotaxesareimposedonprofitsrepatriatedfromtheU.K.toBermuda.ForafurtherdiscussionofthevariousrestrictionsonourabilityandourOperatingSubsidiaries’ ability topaydividends, refer to Item4, “Business Overview—RegulatoryMatters.” Fora discussionof thevolatility andliquidity of our otherinvestments, refer to Item 3D, “Risk Factors —Market and Liquidity Risks,” and for a discussion of the impact of insurance losses on our liquidity, refer toItem3D,“RiskFactors—InsuranceRisks”andItem18,Note15ofourconsolidatedfinancialstatements,“StatutoryRequirementsandDividendRestrictions.”

Operating Subsidiaries.AsatDecember31,2020,theOperatingSubsidiariesheld$1,600.2million(December31,2019—$1,062.7million)incashandshort-term investments that are readily realizable securities. Management monitors the value, currency and duration of cash and investments held by the OperatingSubsidiaries to ensure they are able to meet their insurance and other liabilities as they become due and was satisfied that there was a comfortable margin ofliquidityasatDecember31,2020andfortheforeseeablefuture.

On an ongoing basis, our Operating Subsidiaries’ sources of funds primarily consist of premiums written, investment income and proceeds from sales andredemptions of investments. Cash is used primarily to pay reinsurance premiums, losses and loss adjustment expenses, brokerage commissions, general andadministrativeexpenses,taxes,interestanddividendsandtopurchasenewinvestments.Thepotentialforindividuallargeclaimsandforaccumulationsofclaimsfromsingleeventsmeansthatsubstantialandunpredictablepaymentsmayneedtobemadewithinrelativelyshortperiodsoftime.

Forallmaterialcurrenciesinwhichourunderwritingactivitiesarewrittenweensurethatsufficientcashandshort-terminvestmentsareheldinsuchcurrenciestoenableustomeetpotentialclaimswithoutliquidatinglong-terminvestmentsandadverselyaffectingourinvestmentreturn.Thisfollowsthematchingprinciplewhichmatchesourassetsandliabilitiesincurrencytomitigateforeigncurrencyriskwheneverpossible.

Wemanagetheserisksbymakingregularforecastsofthetimingandamountofexpectedcashoutflowsandensuringthatwemaintainsufficientbalancesincashandshort-terminvestmentstomeettheseestimates. Notwithstandingthispolicy,if thesecashflowforecastsareincorrect, wecouldbeforcedtoliquidateinvestments prior to maturity, potentially at a significant loss. Historically, wehavenot hadto liquidate investments at a significant loss to maintain sufficientlevelsofliquidity.

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Whereweincurlossesincurrencieswhicharenotnormallyheldwewillconvertfundsintotheappropriatecurrenciestomitigateourcurrencyriskandalsomakefunds available to settle claims in local currencies as andwhentheybecomedue. For local regulatory reasons, wehold assets in trusts which limits ourliquiditytosomedegree.Theprocessofmatchingassetswithliabilitiesincurrencymeans,however,thatatanyonetimewewillholdcashandshort-termassetsinallmajorcurrencieswhichareavailabletosettleclaims.

TheliquidityofourOperatingSubsidiariesisalsoaffectedbythetermsofourcontractualobligationstopolicyholdersandbyundertakingstocertainregulatoryauthoritiestofacilitatetheissueoflettersofcreditormaintaincertainbalancesintrustfundsforthebenefitofpolicyholders,orrestrictedforotherreasons.Thefollowing table shows the forms of collateral or other security provided in respect of these obligations and undertakings as at December 31, 2020 andDecember31,2019:

As at December 31, 2020 At December 31, 2019 ($ in millions, except percentages)Regulatorytrustsanddeposits:

Affiliatedtransactions $ 1,027.9 $ 754.9Thirdparty 2,762.2 2,766.6

Lettersofcredit/guarantees 516.8 635.4Totalrestrictedassets(excludingilliquidassets) 4,306.9 0 4,156.9

Otherinvestments—realestatefund(illiquidassets) 109.4 111.4Totalrestrictedassetsandilliquidassets $ 4,416.3 $ 4,268.3Totalaspercentofcashandinvestedassets 58.6% 54.4%

RefertoItem18,Note20(a), “CommitmentsandContingencies—RestrictedAssets”ofourconsolidatedfinancial statementsforfurtherdetail onourtrustfundbalanceswhichwearerequiredtomaintaininaccordancewithcontractualobligationstopolicyholdersandincompliancewithregulatoryrequirements.

Consolidated cash flows for the twelve months ended December 31, 2020.TotalnetcashflowusedinoperationsforthetwelvemonthsendedDecember31,2020was$672.7million,a$334.9millionincreaseincashusedfromtheequivalentperiodin2019.TheincreaseincashusedinoperationsforthetwelvemonthsendedDecember31,2020ismainlyattributablethepurchaseoftheadversedevelopmentcover.ForthetwelvemonthsendedDecember31,2020,thecashflowused in operations required funds to be realized fromthe investment portfolio. Wepaid net claims of $1,764.6 million in 2020 and generated cash inflows of$1,151.2millionfrominvestingduringtheperiod.

Cashflowfromfinancingactivities were $223.5million, includingadditional capital contributionof $268.0million, offset bypreference share dividends of$44.5million.AtDecember31,2020,wehadabalanceofcashandcashequivalentsof$1,747.3million.

Consolidated cash flows for the twelve months ended December 31, 2019.TotalnetcashflowusedinoperationsforthetwelvemonthsendedDecember31,2019was$337.8million,anincreaseof$33.3millionfromtheequivalentperiodin2018.TheincreaseincashusedinoperationsforthetwelvemonthsendedDecember 31, 2019wasmainlyattributable to anincrease in paidclaims. ForthetwelvemonthsendedDecember 31, 2019, thecashflowsusedin operationsrequiredfundstoberealizedfromtheinvestmentportfolio.Wepaidnetclaimsof$2,122.6millionin2019,andgeneratedcashinflowsof$218.3millionfrominvestingduringtheperiod.Weissuedpreferencesharesnetofissuancecostsof$241.6millionandredeemed$125.0millionofour2020SeniorNotes.Wealsopaidpreferencesharedividendsof$35.9million,AtDecember31,2019,wehadabalanceofcashandcashequivalentsof$1,030.5million.

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Capital Resources

Wemaintainourcapitalatanappropriatelevelasdeterminedbyourinternalriskappetiteandthefinancialstrengthrequiredbyourcustomers,regulatorsandratingagencies.Wemonitorandreviewourgroupandoperatingentities’capitalandliquiditypositionsonanongoingbasis.ThefollowingtableshowsourcapitalstructuresasatDecember31,2020comparedtoDecember31,2019:

As at December 31, 2020 At December 31, 2019 ($ in millions)Sharecapital,additionalpaid-incapital,retainedincomeandaccumulatedothercomprehensiveincomeattributabletoordinaryshareholders $ 2,244.1 $ 1,972.0Preferenceshares(liquidationpreferencesnetofissuecosts) 753.5 753.5Long-termdebt 299.9 299.8

Totalcapital $ 3,297.5 $ 3,025.3

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Asat December 31, 2020, total shareholders’ equity was $2,997.6 million compared to $2,725.5 million as at December 31, 2019. Our total shareholders’equityasat December31, 2020includesthreeclassesof preferenceshareswithatotal valueasmeasuredbytheir respectiveliquidationpreferencesof $753.5millionnetofshareissuancecosts(December31,2019—$753.5million,threeclassesofpreferenceshares).

Ourpreferencesharesareclassifiedinourbalancesheetasequitybutmayreceiveadifferenttreatmentinsomecasesunderthecapitaladequacyassessmentsmadebycertainratingagencies.Suchsecuritiesareoftenreferredtoas“hybrids”astheyhavecertainattributesofbothdebtandequity.Managementmonitorstheratioofthetotalofdebtandhybridstototalcapitalwhichwas31.9%asofDecember31,2020(December31,2019—34.6%).Totalcapitalisdefinedasbeingshareholders’equityplusoutstandingdebtandexcludingloannotesissuedbyvariableinterestentities.

Our2023SeniorNotesaretheonlymaterialdebtissuedbyAspenHoldingscurrentlyoutstanding.AsatDecember31,2020and2019,thevalueofdebtlessamortizationexpenseswas$299.9millionand$299.8million,respectively.

Managementmonitorstheratioofdebttototalcapitalwhichwas9.1%asatDecember31,2020(December31,2019—9.8%).

Theprincipalcapitalmanagementtransactionduring2020wasasfollows:

• Duringthefourthquarterof2020,ourparentcompanyHighlandsBermudaHoldco,Ltd.contributedadditionalcapitaltotaling$268.0million.

Theprincipalcapitalmanagementtransactionsduring2019wereasfollows:

• OnAugust13,2019,weissued10,000,000depositaryshares,eachofwhichrepresents1/1000 interestinashareofournewlydesignated5.625%Non-CumulativePreferenceShares.Thedepositaryshareshavealiquidationpreferenceof$25perdepositaryshare(or$250millioninaggregateliquidationpreference).

• On September 30, 2019, we redeemed the remaining $125.0 million of our 2020 Senior Notes due 2020 resulting in a realized loss, or make-wholepaymentof$5.5million.

Access to capital.Ourbusinessoperationsareinpartdependentonourfinancialstrength,theopinionsoftheindependentratingagenciesthereofasdiscussedelsewhere in this report and the market’s perception thereof, as measured by total shareholders’ equity, which was $2,997.6 million as at December 31, 2020(December31,2019—$2,725.5million).Ourabilitytoaccessthecapitalmarketsisdependenton,amongotherthings,ouroperatingresults,marketconditionsand our perceived financial strength. We regularly monitor our capital and financial position, as well as investment and securities market conditions, both ingeneralandwithrespecttoAspenHoldings’securities.OurpreferencesharesanddepositarysharesarelistedontheNYSE.

Letter of Credit Facilities.RefertoItem18,Note23ofourconsolidatedfinancialstatements,“CreditFacilityandLong-termDebt”fordiscussionofourcreditagreementsandletterofcreditfacilities.

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C. Research and Development, Patents and Licenses, etc.

Notapplicable.

D. Trend Information

Throughout2020andinto2021,the(re)insurancemarketexperiencedrateincreases.Althoughthe(re)insurancemarketremainscompetitiveandthereremainsnoshortageofavailablecapital,marketconditionsandratesarestrengthening,whichweexpecttocontinue.Ourowncapitalbasehasbeenbolsteredbythe$268.0millioncapitalcontributionsreceivedfromourshareholderinthefourthquarterof2020.Astherateenvironmentimproves,wewillcontinuetoseekopportunitiesto deploy capital most efficiently to achieve attractive risk-adjusted returns. We have repositioned our portfolio during the last several years and believe ourbusinessiswell-positionedforthecurrentmarketenvironment.Wealsobelievethatstepswehavetakeninrecentyearstostreamlineouroperationsandmanageexpenses combined with this improving rate environment will help us increase our underwriting margins. We remain focused, however, on identifying andcapitalizingonadequatelypricedbusinesswithoutsacrificingunderwritingdiscipline.

COVID-19 is expected to continue to impact global markets. Refer to Item 3D, “Risk Factors” and “Cautionary Statement Regarding Forward-LookingStatements”includedinthisreport.

E. Off-Balance Sheet Arrangements

As at December 31, 2020, we were not party to any off-balance sheet arrangements, as defined by Item 303(a)(4) of Regulation S-K, to which an entityunconsolidatedwithusisapartythatmanagementbelievesisreasonablylikelytohaveacurrentorfutureeffectonourfinancialcondition,revenuesorexpenses,resultsofoperations,liquidity,capitalexpendituresorcapitalresourcesthatwebelieveismaterialtoinvestors.

In November 2016, Peregrine, a subsidiary of the Company, was registered as a segregated accounts company under the Bermuda Segregated AccountsCompanies Act 2000, as amended. As at December 31, 2020, Peregrine had formed six segregated accounts which were funded by third-party investors. ThesegregatedaccountshavenotbeenconsolidatedaspartoftheCompany’sconsolidatedfinancialstatements.

F. Tabular Disclosure of Contractual Obligations

Thefollowingtablesummarizesourcontractualobligations(otherthanourobligationstoemployeesandourPreferenceShares)underlong-termdebt,operatingleases(netofsubleases)andreservesrelatingtoinsuranceandreinsurancecontractsasatDecember31,2020:

2021 2022 2023 2024 2025Later Years Total

($ in millions)Operatingleaseobligations $ 17.2 $ 14.2 $ 13.5 $ 12.6 $ 12.2 $ 63.4 $ 133.1Long-termdebtobligations — — — 300.0 — — 300.0ReservesforlossesandLAE 1,787.7 1,281.0 950.8 716.7 534.6 1,894.6 7,165.3Total $ 1,804.9 $ 1,295.2 $ 964.3 $ 1,029.3 $ 546.8 $ 1,958.0 $ 7,598.4

__________________The long-term debt obligations disclosed above do not include the $14.0 million annual interest payments on our outstanding senior notes or dividendspayabletoholdersofourpreferenceshares.

Inestimatingthetimeintervalsintowhichpaymentsofourreservesforlossesandlossadjustmentexpensesfall,assetoutabove,wehaveutilizedactuariallyassessedpaymentpatterns.Bythenatureoftheinsuranceandreinsurancecontractsunderwhichtheseliabilitiesareassumed,therecanbenocertaintythatactualpaymentswillfallintheperiodsshownandtherecouldbeamaterialaccelerationordecelerationofclaimspaymentsdependingonfactorsoutsideourcontrol.Thetotalamountofpaymentsinrespectofourreserves,aswellasthetimingofsuchpayments,maydiffermateriallyfromourcurrentestimatesforthereasonssetoutunderItem18,Note2ofourconsolidatedfinancialstatements,“CriticalAccountingPolicies—ReservesforLossesandLossExpenses.”

Foradetaileddescriptionofouroperatingleaseobligations,refertoItem18,Note18ofourconsolidatedfinancialstatements,“OperatingLeases.”

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G. Safe Harbor

Cautionary Statement Regarding Forward-Looking Statements

This report contains forward-looking statements within the meaning of Section 27A of the Securities Act of 1933, as amended (the “Securities Act”), andSection21Eof the Securities ExchangeAct of 1934, as amended(the “ExchangeAct”), that are madepursuant to the “safe harbor” provisions of ThePrivateSecuritiesLitigationReformActof1995.Forward-lookingstatementsincludeall statementsthatdonotrelatesolelytohistoricalorcurrentfacts. Inparticular,statements that use the words such as “believe,” “anticipate,” “expect,” “assume,” “objective,” “target,” “plan,” “estimate,” “project,” “seek,” “will,” “may,”“aim,”“likely,” “continue,” “intend,” “guidance,” “outlook,”“trends,” “future,” “could,” “would,”“should,” “target,” “predict,” “potential,” “ontrack”or theirnegativesorvariationsandsimilarterminologyandwordsofsimilarimportgenerallyinvolveforward-lookingstatements.

Allforward-lookingstatementsrelyonanumberofassumptions,estimatesanddataconcerningfutureresultsandeventsthataresubjecttoanumberofrisks,uncertainties,assumptionsandotherfactors,manyofwhichareoutsideourcontrolthatcouldcauseactualresultstodiffermateriallyfromsuchforward-lookingstatements. Accordingly, there are important factors that could cause our actual results to differ materially from those anticipated in the forward-lookingstatements.Webelievethatthesefactorsinclude,butarenotlimitedto,thosesetforthinItem3Dunder“RiskFactors”asthosefactorsmaybeupdatedfromtimeto time in our periodic filings with the United States Securities and Exchange Commission (the “SEC”) which are accessible on the SEC’s website athttp://www.sec.gov.

Theinclusionofforward-lookingstatementsinthisreportshouldnotbeconsideredasarepresentationbyusthatcurrentplansorexpectationswillbeachieved.Forward-lookingstatementsspeakonlyasofthedateonwhichtheyaremadeandweundertakenoobligationtopubliclyupdateorreviseanyforward-lookingstatement,whetherasaresultofnewinformation,futuredevelopmentsorotherwise,exceptasrequiredbylaw.

Effects of Inflation

Inflationmayhaveamaterialeffectonourconsolidatedresultsofoperationsbyitseffectoninterestratesandonthecostofsettlingclaims.Thepotentialexistsafteracatastropheorotherlargepropertyloss,suchashurricanes,forthedevelopmentofinflationarypressuresinalocaleconomyasthedemandforservices,suchasconstruction,typicallysurges.Thecostofsettlingclaimsmayalsobeincreasedbyglobalcommoditypriceinflation.Weseektotakeboththesefactorsintoaccountwhensettingreservesforanyeventswherewethinktheymaybematerial.

Ourcalculationofreservesforlossesandlossexpensesinrespectofcasualtybusinessincludesassumptionsaboutfuturepaymentsforsettlementofclaimsandclaims-handlingexpenses,suchasmedicaltreatmentsandlitigationcosts.WewritecasualtybusinessintheUnitedStates,theUnitedKingdomandAustraliaandcertainotherterritories,whereclaimsinflationhasinmanyyearsrunathigherratesthangeneralinflation.Totheextentinflationcausesthesecoststoincreaseabovereserves established for these claims, wewill be required to increase our loss reserves with a corresponding reduction in earnings. Theactual effects ofinflationonourresultscannotbeaccuratelyknownuntilclaimsareultimatelysettled.

Inadditiontogeneralpriceinflation,weareexposedtoapersistinglong-termupwardstrendinthecostofjudicialawardsfordamages.Weseektotakethisintoaccountinourpricingandreservingofcasualtybusiness.

Wealsoseektotakeintoaccounttheprojectedimpactofinflationonthelikelyactionsofcentralbanksinthesettingofshort-terminterestratesandconsequenteffectsontheyieldsandpricesoffixedinterestsecurities.AsatFebruary2021,althoughinflationiscurrentlylow,weconsiderthatinthemedium-termthereisariskthatinflation,interestratesandbondyieldsmayrise,resultinginadecreaseinthemarketvalueofcertainofourfixedinterestinvestments.RefertoItem3D,“RiskFactors—MarketandLiquidityRisks—Ourresultsofoperationsandinvestmentportfoliomaybemateriallyaffectedbyconditionsimpactingthelevelofinterestratesintheglobalcapitalmarketsandmajoreconomies,suchascentralbankpoliciesininterestratesandtherateofinflation.”

H. Reconciliation of Non-U.S. GAAP Financial Measures

In presenting Aspen's results, management has includedanddiscussed certain “non-GAAPfinancial measures”. Management believes that these non-GAAPfinancialmeasures,whichmaybedefineddifferentlybyothercompanies,betterexplainAspen'sresultsofoperationsinamannerthatallowsforamorecompleteunderstandingoftheunderlyingtrendsinAspen'sbusiness.However,thesemeasuresshouldnotbeviewedasasubstituteforthosedeterminedinaccordancewithGAAP.

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Averageequity, anon-U.S.GAAPfinancial measure, is usedincalculatingordinaryshareholders returnonaverageequity. Averageequityis calculatedbytakingthearithmeticaverageoftotalshareholders’equityonamonthlybasisforthestatedperiodsexcluding(i)theaverageshareofequityduetonon-controllinginterestsand(ii)theaveragevalueofpreferenceshareslessissueexpenses. As at December 31, 2020 As at December 31, 2019 ($ in millions)Totalshareholders’equity $ 2,997.6 $ 2,725.5Non-controllinginterest — —Preferenceshareslessissueexpenses (753.5) (753.5)Averageadjustment (269.4) 182.8Averageequity $ 1,974.7 $ 2,154.8

Accident Year Loss Ratio Excluding Catastrophes and prior year reserve movementsisanon-GAAPfinancialmeasure.Aspenbelievesthatthepresentationoflossratiosexcludingcatastrophesandprioryearreservemovementssupportsmeaningfulcomparisonfromperiodtoperiodoftheunderlyingperformanceofthebusiness.Accidentyearlossratiosexcludingcatastrophesarecalculatedbydividingnetlossesexcludingcatastrophelossesandprioryearreservemovementsbynetearnedpremiumsexcludingcatastrophe-relatedreinstatementpremiums.Aspenhasdefinedcatastrophelossesinthefullyearof2020aslossesassociatedwithCOVID-19,HurricanesIsaiasandLaura,wildfiresinCaliforniaandotherweather-relatedevents.Catastrophelossesinthefullyearof2019weredefinedaslossesassociatedwithHurricaneDorian,TyphoonsFaxaiandHagibisinJapan,andotherweather-relatedeventsinIndia,AustraliaandtheU.S.

Twelve Months Ended December 31, 2020Accident year ex CAT ratio Reinsurance Insurance Total ($ in millions)Netearnedpremium $ 1,292.1 $ 1,240.5 $ 2,532.6Lossesandlossadjustmentexpenses 958.6 882.2 1,840.8Prioryearreservemovements (36.1) 35.2 (0.9)Catastrophelosses(includingCOVID-19losses) 244.0 116.8 360.8Lossesexcludingcatastrophesandprioryearreservemovements 750.7 730.2 1,480.9AccidentyearexCATratio 58.1% 58.9% 58.5%

Twelve Months Ended December 31, 2019Accident year ex CAT ratio Reinsurance Insurance Total ($ in millions)Netearnedpremium $ 1,255.2 $ 1,038.1 $ 2,293.3Lossesandlossadjustmentexpenses 917.9 761.8 1,679.7Prioryearreservemovements (54.9) 114.4 59.5Catastrophelosses 125.1 244.0 18.1 244.0 143.2Lossesexcludingcatastrophesandprioryearreservemovements 847.7 629.3 1,477.0AccidentyearexCATratio 67.4% 60.7% 64.3%________________

Netofreinstatementpremiums

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Accident year ex-catastrophe combined ratiois anon-GAAPfinancial measureandis calculatedasthesumoftheAccident year exCATlossratioandtheexpenseratio.In2020,wehaveincludedlossesassociatedwithCOVID-19totaling$181.2million(2019—$Nil)withincatastrophelosses.

Twelve Months Ended December31, 2020

Twelve Months Ended December31, 2019

($ in millions)Accidentyearex-catastrophelossratio 58.5 % 64.3 %Expenseratio 34.6 % 40.7 %Accidentyearex-catastrophecombinedratio 93.1 % 105.0 %

Retention ratioisanon-GAAPfinancialmeasureandiscalculatedbydividingnetwrittenpremiumsbygrosswrittenpremiums.Twelve Months Ended December 31, 2020 Twelve Months Ended December 31, 2019

Retention ratio Reinsurance Insurance Total Reinsurance Insurance Total ($ in millions)

Grosswrittenpremium 1,660.8 2,042.8 3,703.6 1,485.5 1,956.9 3,442.4Netwrittenpremium 1,302.1 1,280.8 2,582.9 1,251.1 1,176.8 2,427.9Retentionratio 78.4 % 62.7 % 69.7% 84.2 % 60.1 % 70.5%

Underwriting profit or loss/ gain or loss isanon-GAAPfinancialmeasure.Profitorlossforeachofthebusinesssegmentsismeasuredbyunderwritingprofitorloss.Underwritingprofitorlossistheexcessofnetearnedpremiumsoverthesumoflossesandlossexpenses,amortizationofdeferredpolicyacquisitioncostsandgeneralandadministrativeexpenses.Underwritingprofitorlossprovidesabasisformanagementtoevaluatethesegment’sunderwritingperformance.

Book yield isanon-GAAPfinancialmeasure.Bookyieldistheinterestrateearned,atthetimeofpurchaseofthefixedincomeinstrumentatmarketvalue,assumingthebondisheldtomaturityandallcouponandprincipalpaymentsaremadeonschedule.

General Insurance:

Along with most property and casualty insurance companies, we use the loss ratio, the expense ratio and the combined ratio as measures of underwritingperformance.Theseratiosarerelativemeasurementsthatdescribe,forevery$100ofnetpremiumsearned,theamountoflossesandlossadjustmentexpenses,andtheamountofotherunderwritingexpensesthatwouldbeincurred.Acombinedratiooflessthan100indicatesunderwritingincomeandacombinedratioofover100 indicates an underwriting loss. Combined ratios differ from U.S. statutory combined ratios primarily due to the deferral of certain third-party acquisitionexpensesforGAAPreportingpurposesandtheuseofnetpremiumsearnedratherthannetpremiumswritteninthedenominatorwhencalculatingtheacquisitionexpenseandthegeneralandadministrativeexpenseratios.

Combined Ratio (excluding non-operating expenses) Twelve Months Ended(inUS$millionsexceptwherestated) December 31, 2020 December 31, 2019

Numerator: Sum of:Lossesandlossadjustmentexpenses 1,840.8 1,679.7Amortizationanddeferredpolicyacquisitioncosts 465.7 412.7General,administrativeandcorporateexpenses 378.2 396.0Non-operatingexpenses 32.7 125.6Numerator total 2,717.4 2,614.0

Denominator:Netearnedpremiums 2,532.6 2,293.3

Combinedratio 107.3% 113.9%

Adjustments to numerator:Excludenon-operatingexpenses (32.7) (125.6)Numeratortotal-excludingnon-operatingexpenses 2,684.7 2,488.4

Combined ratio (excluding non-operating expenses) 106.0% 108.5%

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Thefollowingtablespresentsupplementaryfinancialinformationregardingourtworeportingsegments,ReinsuranceandInsurance,asatDecember31,2020andDecember31,2019,toshowtheimpactonourfinancialperformancefromthebusinesswhichwehaveceasedunderwritingandhasbeenclassifiedas“Legacy”.“Legacy”businessinthe2019tablehasbeenrepresentedonalikeforlikebasis,meaningallthesamelinesofbusinesshavebeenincludedasLegacyinboththe2020and2019tables,notwithstandingthatcertainlinesofbusinesswerenotyetclassifiedasLegacyasatDecember31,2019(e.g.SuretyInsuranceandcertainU.S.CropandAgriculturalBusiness).Webelievethispresentationprovidesforamorecompleteunderstandingoftheimpactthattheselinesofbusinesshavehadonourunderlyingperformance.

Twelve Months Ended December 31, 2020Reinsurance Insurance

OngoingReinsurance Legacy Reinsurance Total

OngoingInsurance Legacy Insurance Total Group Total

Netearnedpremiums 1,008.5 283.6 1,292.1 1,083.7 156.8 1,240.5 2,532.6Lossesandlossadjustmentexpenses 711.9 246.7 958.6 730.8 151.4 882.2 1,840.8Amortizationofdeferredpolicyacquisitionexpenses 216.0 30.0 246.0 172.7 47.0 219.7 465.7Generalandadministrativeexpenses 107.3 3.5 110.8 179.5 17.7 197.2 308.0Underwriting(loss)/gain $ (26.7) $ 3.4 $ (23.3) $ 0.7 $ (59.3) $ (58.6) $ (81.9)

Corporateexpenses (70.2)Non-operatingexpenses (32.7)Netinvestmentincome 154.6Realizedandunrealizedinvestmentgains 98.5Realizedandunrealizedinvestmentlosses (27.4)Realizedlossondebtextinguishment —Changeinfairvalueofloannotesissuedbyvariableinterestentities —Changeinfairvalueofderivatives (65.1)Interestexpenseonlongtermdebt (33.9)Netrealizedandunrealizedforeignexchange(losses) (12.4)Otherincome 49.8Otherexpenses (10.8)(Loss) before tax (31.5)Incometax(expense) (8.6)Net (loss) $ (40.1)RatiosLossratio 70.6 % 87.0 % 74.2 % 67.4 % 96.6 % 71.1 % 72.7 %Policyacquisitionexpenseratio 21.4 % 10.6 % 19.0 % 15.9 % 30.0 % 17.7 % 18.4 %Generalandadministrativeexpenseratio 10.6 % 1.2 % 8.6 % 16.6 % 11.3 % 15.9 % 16.2 %Expenseratio 32.0 % 11.8 % 27.6 % 32.5 % 41.3 % 33.6 % 34.6 %Combinedratio 102.6 % 98.8 % 101.8 % 99.9 % 137.9 % 104.7 % 107.3 %Accident Year Ex-cat Loss RatioLossratio 70.6 % 87.0 % 74.2 % 67.4 % 96.6 % 71.1 % 72.7 %Prioryearlossdevelopment 3.4 % 0.8 % 2.8 % (0.5) % (19.0)% (2.8)% 0.0 %Current Year AdjustmentsCatastrophelosses (11.4) % 0.0 % (8.9) % (5.9) % (0.2)% (5.2)% (7.1)%COVID-19losses (12.4) % (1.2)% (10.0) % (2.8) % (13.9)% (4.2)% (7.1)%Accident year ex-cat loss ratio 50.1 % 86.6 % 58.1 % 58.2 % 63.5 % 58.9 % 58.5 %

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Legacyreflectsbusinesswehaveelectedtoceaseunderwritingfollowingaseriesofstrategicunderwritingreviews.

Legacy(reinsurance)represents:(i)U.S.cropinsurancebusinesswhichwaspreviouslywrittenonareinsurancebasisthroughastrategicpartnershipuntildisposedofinQ42020;(ii)ourglobalcreditandsuretyreinsurancebusinessthatweceasedunderwritingduringQ32019;and(iii)andourU.S.AgriculturalbusinesswrittenviaAgriLogicwhichwassoldinDecember2017.

Legacy(insurance)represents:

(i)U.S.suretybusiness,whichinJuly2020wassubjecttoarenewalrightstransaction;(ii)includesinternationalmarineandenergyliabilityproducts,andourglobalaccidentandhealthlineofbusiness,which,followingastrategicreviewofourunderwritingportfoliothatbeganinDecember2019,wedeterminedtoceaseunderwritingandstartedtowinddowninFebruary2020andMarch2020,respectively;(iii) professional liability and property and casualty coverages for small to medium sized U.K.-based businesses that was bound through our managing general agent, Aspen RiskManagementLimitedthatweplacedintorunoffduringQ32019;(iv)internationalcargoinsurancethatweceasedunderwritingduringQ42018;(v)ouraviationlineofbusiness,whichwedecidedtoceaseunderwritingduringQ32018;(vi)marinehullinsurancewrittenthroughtheLloyd’splatformthatweceasedunderwritingduringQ32018;(vii)internationalpropertyinsurancepreviouslywrittenviaajointunderwritinginitiativethatweceasedunderwritingduringQ12017;and(viii)employersandpublicliabilitylinespreviouslywrittenthatweceasedunderwritingduringQ42015.

Non-operatingexpensesincludes$18.2millionofcostsrelatedtoseverance,retentionawards,amortizationofintangibleassetsandothercosts,$12.9millionofimpairmentchargesrelatedtoleaseassetsasaresultofsub-leasingcertainofficespaceand$1.6millionofothernon-operatingexpenses.

Thegeneralandadministrativeexpenseratiointhetotalcolumnincludescorporateandnon-operatingexpenses.

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Twelve Months Ended December 31, 2019Reinsurance Insurance

OngoingReinsurance Legacy Reinsurance Total OngoingInsurance Legacy Insurance Total Group Total

Netearnedpremiums 862.3 392.9 1,255.2 807.3 230.8 1,038.1 2,293.3Lossesandlossadjustmentexpenses 572.7 345.1 917.9 510.8 251.1 761.8 1,679.7Amortizationofdeferredpolicyacquisitionexpenses 199.5 65.5 264.9 100.3 47.4 147.8 412.7Generalandadministrativeexpenses 103.5 8.2 111.7 176.9 52.9 229.8 341.5Underwriting(loss)/gain $ (13.4) $ (25.9) $ (39.3) $ 19.3 $ (120.6) $ (101.3) $ (140.6)

Corporateexpenses (54.5)Non-operatingexpenses (125.6)Netinvestmentincome 197.3Realizedandunrealizedinvestmentgains 97.1Realizedandunrealizedinvestmentlosses (10.9)Realizedlossondebtextinguishment (5.5)Changeinfairvalueofloannotesissuedbyvariableinterestentities (3.1)Changeinfairvalueofderivatives (144.2)Interestexpenseonlongtermdebt (20.2)Netrealizedandunrealizedforeignexchange(losses) (11.8)Otherincome 4.9Otherexpenses (1.7)(Loss) before tax (218.8)Incometax(expense) (22.9)Net (loss) $ (241.7)RatiosLossratio 66.4 % 87.8% 73.1 % 63.3 % 108.8% 73.4% 73.2%Policyacquisitionexpenseratio 23.1 % 16.7% 21.1 % 12.4 % 20.5% 14.2% 18.0%Generalandadministrativeexpenseratio 12.0 % 2.1% 8.9 % 21.9 % 22.9% 22.1% 22.7%Expenseratio 35.1 % 18.8% 30.0 % 34.3 % 43.4% 36.3% 40.7%Combinedratio 101.5 % 106.6% 103.1 % 97.6 % 152.2% 109.7% 113.9%Accident Year Ex-cat Loss RatioLossratio 66.4 % 87.8% 73.1 % 63.3 % 108.8% 73.4% 73.2%Prioryearlossdevelopment 5.6 % 1.8% 4.4 % (1.4) % (44.7)% (11.0)% (2.6)%Catastrophelosses (15.2) % —% (10.1) % (1.9) % (0.5)% (1.7)% (6.3)%Accident year ex-cat loss ratio 56.8 % 89.6% 67.4 % 60.0 % 63.5% 60.7% 64.3%

_______________Legacyreflectsbusinesswehaveelectedtoceaseunderwritingfollowingaseriesofstrategicunderwritingreviews.

Legacy(reinsurance)represents:(i)U.S.cropinsurancebusinesswhichwaspreviouslywrittenonareinsurancebasisthroughastrategicpartnershipuntildisposedofinQ42020;(ii)ourglobalcreditandsuretyreinsurancebusinessthatweceasedunderwritingduringQ32019;and(iii)andourU.S.AgriculturalbusinesswrittenviaAgriLogicwhichwassoldinDecember2017.

Legacy(insurance)represents:

(i)U.S.suretybusiness,whichinJuly2020wassubjecttoarenewalrightstransaction;(ii)includesinternationalmarineandenergyliabilityproducts,andourglobalaccidentandhealthlineofbusiness,which,followingastrategicreviewofourunderwritingportfoliothatbeganinDecember2019,wedeterminedtoceaseunderwritingandstartedtowinddowninFebruary2020andMarch2020,respectively;(iii) professional liability and property and casualty coverages for small to medium sized U.K.-based businesses that was bound through our managing general agent, Aspen RiskManagementLimitedthatweplacedintorunoffduringQ32019;(iv)internationalcargoinsurancethatweceasedunderwritingduringQ42018;(v)ouraviationlineofbusiness,whichwedecidedtoceaseunderwritingduringQ32018;(vi)marinehullinsurancewrittenthroughtheLloyd’splatformthatweceasedunderwritingduringQ32018;(vii)internationalpropertyinsurancepreviouslywrittenviaajointunderwritinginitiativethatweceasedunderwritingduringQ12017;and(viii)employersandpublicliabilitylinespreviouslywrittenthatweceasedunderwritingduringQ42015

Non-operating expenses includes $103.4 million of costs related to the Merger, severance, retention and other costs, $22.2 million of expenses related to the Company’s operatingeffectivenessandefficiencyprogram,whichincludes$12.3millionofimpairmentchargesrelatedtoleaseassetsasaresultofsub-leasingcertainofficespace.

Thegeneralandadministrativeexpenseratiointhetotalcolumnincludescorporateandnon-operatingexpenses.

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Item 6.Directors, Senior Management and Employees

A. Directors and Senior Management

ThefollowingarethedirectorsandseniormanagementoftheCompanyasofthedateofthisreport.

Name Position with the Company Date AppointedDirectorsMarkCloutier GroupChiefExecutiveOfficer,ExecutiveChairmanoftheBoardandChairoftheRiskCommittee February2019AlbertJ.Beer Director,MemberofAudit,ConflictsandRiskCommittees July2019JoshuaBlack Director,MemberofRiskCommittee February2019TheresaFroehlich Director,ChairofConflictsCommittee June2020AlexHumphreys Director,MemberofRiskCommittee February2019GordonIreland Director,ChairofAuditCommittee,MemberofConflictsandRiskCommittees February2013RichardLightowler Director December2020GernotLohr Director February2019TammyL.Richardson-Augustus Director March2021MichaelSaffer Director,MemberofRiskCommittee February2019Senior ManagementMarkCloutier GroupChiefExecutiveOfficerandExecutiveChairmanoftheBoard February2019KevinChidwick GroupChiefFinancialOfficer May2020BryanAstwood GroupChiefInvestmentOfficer May2019MichaelCain GroupGeneralCounsel,CompanySecretaryandGroupChiefOperatingOfficer March2008BruceEisler ChiefUnderwritingOfficerofAspenInsuranceandChiefExecutiveOfficerofAspenU.S. June2020

ChristianDunleavyChiefUnderwritingOfficerofAspenRe,ChiefExecutiveOfficerandChiefUnderwritingOfficerofAspenBermuda May2019

MohinderKang GroupChiefPeopleandTransformationOfficer November2019RichardMilner ChiefExecutiveOfficerofAspenU.K. February2020BrianTobben ChiefExecutiveOfficerofAspenCapitalMarkets June2020

(1)Mr.BeerpreviouslyservedasaDirectoroftheCompanyfromFebruary4,2011untilFebruary15,2019.

Mr.Irelandwillnotstandforre-electionattheCompany’s2021AnnualGeneralMeetinganditisanticipatedthatMr.LightowlerwillsucceedMr.IrelandasChairoftheAuditCommitteefollowingthe2021AnnualGeneralMeeting.

Mr.AstwoodwillretirefromtheCompanyonJune17,2021.

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Biographical informationDirectors:• Mark Cloutier, Group Chief Executive Officer, Executive Chairman of the Board and Chair of the Risk Committee

Mr.Cloutier wasappointedExecutiveChairmanandGroupChiefExecutiveOfficer ofAspenonFebruary15, 2019.MarkhadpreviouslybeenExecutiveChairman of the Brit Group since January 2017 and prior to this, he was Chief Executive Officer of the Group from October 2011. As Chief ExecutiveOfficer,Mr.CloutierledamajorrestructuringofBrits'globalbusiness,thesuccessfullistingontheLondonstockexchangethroughaninitialpublicofferingin2014aswellasthesubsequentacquisitionofthebusinessbyFairfaxFinancialHoldingsin2015.Withover35years’experienceworkingintheinternationalinsuranceandreinsurancesectorinmultiplejurisdictionsincludingCanada,theUnitedStates,theUnitedKingdom,Bermuda, Continental Europe, Asia, ChinaandSouthAfrica, Markhashelda numberof CEOandsenior executivepositions, includingCEOoftheAleaGroup,CEOofOverseasPartnersReandPresidentofE.W.BlanchInsuranceServicesInc.HehadbeenamemberoftheFranchiseBoardandAuditCommitteeoftheSocietyofLloyd'sbetweenFebruary2015andJune2020andwasappointedtotheNominationandGovernanceCommitteeinFebruary2017.MarkhasworkedwithavarietyofprivateequityinvestorsincludingApolloManagementInternationalLLP,CVCCapitalPartners,KohlbergKravisRoberts(KKR)andFortress.HestartedhiscareerinBritishColumbiaCanadawithBrouwerandcompanyindependentlossadjustersbeforemovingontoformhisownfirm,MaxwellCloutierAdjustersLtd.

• Albert J. Beer, Independent Director and Member of the Audit, Conflicts and Risk Committees

Mr.Beerhasover40yearsofactuarialandmanagementexperienceintheinsuranceindustryandhasalsoservedasadirectorofAspenBermudaLimitedsince July 2014. Mr. Beer previously held various Executive roles at American Re-Insurance Corporation/Munich Re America, which included the activesupervision of principal financial and accounting officers. Mr. Beer is the Michael J. Kevany/XLProfessor of Risk Management, Insurance and ActuarialScienceatThePeterJ.TobinCollegeofBusinessSchoolofRiskManagement,InsuranceandActuarialScienceatSt.John'sUniversity.Mr.BeergraduatedPhi Betta Kappa fromManhattan College with a B.S. in Mathematics and holds an M.A. in Mathematics fromthe University of Colorado. Mr. Beer wasappointedtotheBoardonJuly23,2019afterhavingpreviouslyservedontheBoardfromFebruary4,2011untilFebruary15,2019.

• Joshua Black, Director and Member of the Risk Committee

Mr.BlackisaPrincipalinApollo’sPrivateEquitydivision,havingjoinedApolloin2011.Mr.Blackfocusesonawiderangeofindustries,includingpropertyandcasualtyinsurance.PriortojoiningApollo,Mr.BlackwasamemberoftheLeveragedFinanceProductGroupatGoldmanSachs&Co.,havingworkedpreviously in the Financial Institutions Industry Group. Mr. Black currently sits on the board of Sun Country Airlines, Tegra, Huddle House, Volotea,SomersetPartners,AugustusSpecialty,PacificQuickServe(BKFranchisee),andESW.Mr.BlackpreviouslyservedontheboardofExelaTechnologiesInc.Mr.BlackgraduatedcumlaudefromPrincetonUniversitywithaB.A.inReligion.

• Theresa Froehlich, Independent Director and Chair of the Conflicts Committee

Ms.FroehlichhasbeenadirectoroftheCompanysinceJune11,2020.Shehasover25yearsofmanagementexperienceinthefinancialservicesindustry.From2010to2016,Ms.FroehlichheldseniorrolesatthespecialistLloyd’sofLondoninsuranceandreinsurancemarketplace,includinginterimdirectorofperformancemanagement,whereshewasresponsibleforallcommercialaspectsofoversightofthemarketplaceandsettingunderwritingstandards,andalsoheadofunderwritingperformance.BeforeLloyd’s,sheworkedinZurichasaManagingDirectorforSwissReinvariousroles.Havingstartedthereinprivateequity, she later took on senior management roles which included portfolio management of structured reinsurance products, driving transformation andstrategicinitiativesandservingastheHeadofTransactionsUKatAdminRe.ShecurrentlyservesastheSeniorNon-executiveDirectorofScottishEquitablePlc,andasaNon-executiveDirectorandChairoftheAuditCommitteeofManagingAgencyPartnersLtd.since2017andservedaNon-executiveDirectorofStarrInternationalEuropeLimitedandStarrManagingAgentsLimitedfrom2017-2020whereshechairedtheRemunerationCommitteeandwasamemberofthe Audit and Risk Committees. In addition, Ms. Froehlich has served as the Chair of Aspen Insurance U.K. Limited and as a Non-executive Director ofAspenManagingAgencyLimited,whereshealsochairstheRiskCommittee,sinceNovember2019.Ms.FroehlichstartedhercareerasacommercialsolicitorinScotlandbeforemovingintoM&Aandstructuredfinance.

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• Alex Humphreys, Director and Member of the Risk Committee

Mr.HumphreysisaPartnerat Apollo,whichhejoinedin2008.Priortothis, Mr.HumphreysworkedatGoldmanSachsinitsfinancial institutionsM&Ateam.Mr.HumphreysalsocurrentlyservesontheboardsofvariousApolloportfoliocompaniesincludingAthoraHolding,Ltd,CatalinaHoldings(Bermuda)Ltd.,LuminescenceCooperatiefU.A.,andAmissimaHoldings,S.r.l.HepreviouslyservedontheboardofdirectorsofHDFinanceHoldingsLimited(parentofHaydockFinanceHoldingsLimited),LatecoereS.A.,andSeguradorasUnidasS.A.(parentofTranquilidade).HewasappointedasaDirectoroftheBoardonFebruary15,2019and,omadditiontobeingamemberoftheCompensationandRiskCommittees,heisalsoamemberoftheboardofHighlandsBermudaHoldco,Ltd.,HighlandsManco,Ltd.andHighlandsHoldingsBondIssuer,Ltd.

• Gordon Ireland, Independent Director, Chair of the Audit Committee and Member of the Conflicts and Risk Committees

Mr.Irelandhasover35yearsofexperiencewithinthefinancialservicessector,havingworkedatPricewaterhouseCoopersanditspredecessorfirmsfor36years until 2010, wherehewasalsoa member of theU.K.Firms' SupervisoryBoardfor nineyears. FromJuly2010until June2015, Mr. Irelandwasadirector of L&F Holdings Limited and Chief Executive of L&F Indemnity Limited, the professional indemnity captive insurance group which serves thePricewaterhouseCoopersnetwork.Mr.IrelandhasheldanumberofdirectorshipsontheboardsoffinancialinstitutionsandiscurrentlyadirectorofYorkshireBuildingSociety.Asaresultofhisaudit-ledexposuretotheLondonMarketandgeneralinsuranceandreinsurancemarketsthroughouthiscareer,Mr.IrelandprovidesstronginsuranceauditskillsandtechnicalaccountancyexpertisetoourBoard.Asaresult,heservesasChairoftheAuditCommittee,onwhichheisalsoadesignatedfinancialexpert,andasamemberoftheRiskCommittee.Mr.IrelandgraduatedwithHonorsfromSouthamptonUniversitywithaBScinMathematics.Mr.IrelandwasappointedasaDirectoroftheBoardonFebruary7,2013.

• Richard Lightowler, Independent Director

Mr.Lightowlerhasover25years’experienceinfinancialservicespublicaccountingfocusedonreinsuranceandinsuranceclients,includingnon-lifeandlife,primaryandreinsurance,run-offaswellasspecializedriskvehicles,includingILSstructuresandsegregatedcellcompanies.HewasaPartnerwithKPMGfrom1998to2016,wherehespentover16yearsservingasgloballeadauditpartnerforSECregistrantsandaswellasreinsurancegroupslistedontheLondonStockExchange.HealsoservedasHeadoftheKPMGBermudaInsurancePractice.Hehassignificantprivateandpublicequityanddebtofferingexperienceandhasworkedonanumberofcross-bordermergersandacquisitionsincludingBuy-side/Sell-sideduediligence,structuringandpost-acquisitionintegration.Mr.LightowleriscurrentlyaNon-ExecutiveDirectorofHansaInvestmentCompanyLimited,GenevaReLimited,OakleyCapitalInvestmentsLimited,SomersfieldAcademyandBermudaRedCross.Mr.LightowlerwasappointedasaDirectoroftheBoardonDecember10,2020.

• Gernot Lohr, Director

Mr.LohrisaSeniorPartnerandGlobalHeadoftheFinancialInstitutionsGroupatApollo,whichhejoinedinMay2007.PriortojoiningApollo,Mr.LohrwasafoundingpartneratInfinityPointLLC,Apollo’sjointventurepartnerforthefinancialservicesindustry,since2005.Beforethattime,Mr.Lohrspenteight years in financial services investment banking at Goldman Sachs & Co in New York and also worked at McKinsey & Company and B. MetzlerCorporate Finance in Frankfurt. Currently, Mr. Lohr serves on the board of directors of Athora Holding, Ltd., Catalina Holdings and OldenburgischeLandesbank. Mr. Lohr has previously served on the board of directors of Tranquilidade, Amissima Vita S.p.A., Amissima Assicurazioni S.p.A., BremerKreditbankAktiengesellschaft,NovaKreditnabankaMaribord.d.andKBSBankad.d.Mr.LohrhasajointMaster’sDegreeinEconomicsandEngineeringfromtheUniversityofKarlsruhe,Germany,andreceivedaMastersinBusinessAdministrationfromtheMITSloanSchoolofManagement.

• Tammy L. Richardson-Augustus, Independent Director

Ms.Richardson-Augustushasover20yearsoflegal experienceandsince2007hasbeenapartnerandamemberoftheBermudacorporatedepartmentofAppleby,aleadingglobalproviderofoffshorelegalandfiduciaryservices.Ms.Richardson-Augustusprovidestransactionalandcorporategovernanceadvicetocorporateclients(includingbutnotlimitedtodevelopingaframeworkofprudentandeffectivepoliciesforboardcommittees).Ms.Richardson-Augustusmaintainsadiversifiedbusinesstransactionspractice,withemphasisondomesticandinternationalmergersandacquisitions,jointventures,capitalmarketsandsecurities,securedandunsecuredlendingtransactionsandgeneralcorporategovernancematters.Shehasextensiveexperienceworkingwithclientsinawiderangeofindustries,includinginenergy,oilandgasexploration,andmaritimeshipping.Ms.Richardson-Augustuscurrentlyservesonnumerousboardsincluding,interalia,onthestatutoryboard(BermudaDepositInsuranceCorporation)andontheboardofPolaris(a

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companylistedontheBermudastockexchange)andisamemberoftheBermudaBarAssociationandisajusticeofthepeace.

• Michael Saffer, Director and Member of the Risk Committee

Mr.SafferisaPrincipalintheLondonPrivateEquityteamatApollo,havingjoinedin2015.PriortojoiningApollo,hewasamemberoftheM&AgroupatCredit SuisseinLondon.Mr.SafferhasbeeninvolvedinvariousprivateequitytransactionsincludingApollo’sacquisitionofOldenburgischeLandesbank(formerlyknownasBremerKreditbankAG),CatalinaHoldings(Bermuda)Ltd.,AspenInsuranceHoldingsLimitedandCovisGroupS.a.r.l.Mr.SafferwasappointedasaDirectoroftheBoardonFebruary15,2019andisalsoamemberoftheboardsofHighlandsBermudaHoldco,Ltd.,HighlandsManco,Ltd.,HighlandsHoldingsBondIssuer,Ltd.,CovisGroupS.a.r.l.andGamenetGroupS.p.A.Mr.SaffergraduatedfromtheUniversityofNottinghamwithaBScinEconomics.

Senior Management

• Mark Cloutier, Group Chief Executive Officer and Executive Chairman of the Board

SeeMr.Cloutier’sBiographicalInformationunderDirectorsabove.

• J. Bryan Astwood, Group Chief Investment Officer

Mr.AstwoodhasservedasAspen’sGroupChiefInvestmentOfficersince2009andasitsGroupRepresentativetotheBMAfrom2014toJuly2020.Hehasover30yearsofexperienceinthefixedincome,equity,foreignexchangeandcommoditymarkets,havingbegunhiscareerattheBankofBermuda.Priortojoining Aspen in 2003 as Group Treasurer, he worked at Bank of America in Hong Kong, Industrial Bank of Japan in Tokyo and Butterfield AssetManagementandOrbisInvestmentManagementinBermuda.

• Michael Cain, Group General Counsel, Company Secretary and Group Chief Operating Officer

Mr.CainjoinedtheCompanyasGroupGeneral CounselandCompanySecretaryinMarch2008andservedinthiscapacityuntil May2019whenhewasappointedGroupChiefOperatingOfficer.InMarch2020,heresumedhisroleasGroupGeneralCounselandCompanySecretaryinadditiontoGroupChiefOperatingOfficer.Mr.CainalsopreviouslyservedasChiefExecutiveOfficerofbothAspenU.K.andAMALandpriortothat,heservedasChiefExecutiveOfficerofAspenBermuda.PriortojoiningtheCompany,Mr.CainservedasCorporateCounselandCompanySecretarytoBenfieldGroupLimitedfrom2002to2008andhasworkedatlawfirmsBarlowLyde&GilbertLLPandAshurstLLP.

• Kevin Chidwick, Group Chief Financial Officer

Mr.ChidwickwasappointedGroupChiefFinancialOfficer,effectiveMay1,2020.Mr.ChidwickwaspreviouslyChiefFinancialOfficeratfinancialadvicenetworkOpenworkLimited,arolehewasappointedtoinMarch2018.FromSeptember2005toAugust2014,Mr.ChidwickwasChiefFinancialOfficerofAdmiral Group Plc. He was appointed to the Admiral Group Plc Board in 2006. He also held senior roles within the Admiral Group Plc including ChiefExecutiveOfficerofElephantAutoInsuranceintheU.S.fromJanuary2012toMarch2017,wherehegrewannualrevenuefrom$17millionto$200million,andChiefExecutiveOfficerofConfused.comfromNovember2010toDecember2011.

• Christian Dunleavy, Chief Underwriting Officer of Aspen Re and CEO and Chief Underwriting Officer of Aspen Bermuda

Mr. Dunleavy joined Aspen in 2015 as Head of Global Property Catastrophe. He was appointed as Chief Underwriting Officer of Aspen Re and CEOofAspenBermudainMay2019.HehasalsoservedasChiefUnderwritingOfficerofAspenBermudaLimitedsinceMay2017.Mr.DunleavyjoinedAspenReinSeptember2015asHeadofGlobalPropertyCatastrophe.HehadpreviouslybeenatAxisReinsurancewherehewasaSeniorVicePresident,responsiblefor U.S. Property Treaty, CaribbeanProperty andWorkers CompensationCatastrophebusiness. Prior to joiningAxis in 2002, Mr. Dunleavywasa SeniorAnalystatRenaissanceRe,responsibleformulti-perilmodeling,pricingandportfolioanalysis.Mr.DunleavyisalsoaDirectoroftheAssociationofBermudaInternationalCompanies,theAssociationofBermudaInsurersandReinsurersandanIndependentDirectorofColonialGroupInternational.

• Bruce Eisler, Chief Executive Officer U.S. and Chief Underwriting Officer, Aspen Insurance

Mr.EislerwasappointedChiefExecutiveOfficerU.S.andChiefUnderwritingOfficer,AspenInsuranceinJune2020.Mr.EislerhasheldvariousseniorlevelroleswithRelianceNational,ACEUSAandLibertyInternationalUnderwriters—part

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ofLibertyMutualGroup—wherehewastheSeniorVicePresidentofProfessionalLiabilityUnderwritingbeforejoiningAspeninJanuary2010.

• Mohinder (Mo) Kang Group Chief People and Transformation Officer

Mr.KangjoinedtheCompanyasChiefPeopleOfficerinNovember2019andsubsequentlytookonresponsibilityfortheGroupCommunicationsfunctioninJune 2020. In January 2021, he was appointed Chief People & Transformation Officer and he currently leads Aspen’s HR function and TransformationProgram.PriortojoiningAspenhewasemployedbytheUKPostOfficewherehewasGroupHRDirector.Mr.Kang’sextensiveexperienceincludesleadingsignificant HR,Communication andchangeprogramsandteams, andhasworkedas part of several Executive teamsfor the past 25years across differentbusiness sectors. Mr. Kanghad previously served as GroupHRand Corporate Communications Director at Hyperion Insurance Groupfor twoyears, andGroupChiefHumanResourcesOfficeratQBEInsuranceGroupfor10years,aswellasOrganisationDevelopmentDirectoratZurichFinancialServicesforeightyears.

• Richard Milner, Chief Executive Officer, Aspen U.K. and AMAL

Mr.MilnerwasappointedChiefExecutiveOfficerofAspenU.K.andAMALinJune2020.Mr.Milnerhasmorethan20yearsofexperienceacrossanumberofglobal (re)insurancemarkets havingworkedinLondon,BermudaandSingapore. Overhiscareer Mr. Milnerhasgainedunderwritingexperienceacrossmultipleproductlinesandinallareasofmanagement,leadership,capitalplanningandunderwriting.PriortojoiningAspen,hewasChiefExecutiveOfficeratVIBERe,thereinsuranceoperationofVIBESyndicate.HehasalsoservedinseniorpositionsatAXISCapital,includingPresidentandChiefUnderwritingOfficer,AXISReLondonandAPAC,andHeadofGlobalBusinessDevelopment,AXISRe.

• Brian Tobben, Chief Executive Officer, Aspen Capital Markets

Mr.TobbenwasappointedChiefExecutiveOfficerofAspenCapital Markets, adivisionofAspen,inJune2020.Priortothis, heservedastheManagingDirectorforAspenCapitalMarketssincehejoinedAspeninApril2013.BeforejoiningAspen,Mr.TobbenwasatPartnerReinsuranceforalmost10years,most recentlyasHeadofInsuranceLinkedSecurities wherehemanagedaportfolioofcatastropheILS,life ILS,weatherandcommodityinvestments andbeforethat,asVicePresident,Weather.Priortothis,Mr.TobbenwasatAquilaEnergywhereheheldanumberofrolesincludingVicePresident,BusinessDevelopment,Weather.

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B. Compensation

Director Compensation

The Company paid approximately $1.3 million as aggregate compensation to non-executive directors for their services during 2020. This includescompensation paid to Mr. John Cavoores, who resigned from the Board effective October 15, 2020 and Mr. Bruce Hemphill, who resigned from the BoardeffectiveFebruary5,2021.InthecaseofMessrs.BeerandIrelandandMs.Froehlich,thisalsoincludesfeespaidfortheirservicesasdirectorsofcertainoftheCompany’ssubsidiaries.

Mr.Cloutier,ourGroupChiefExecutiveOfficerandExecutiveChairmanoftheBoarddidnotreceiveanycompensationforhisservicesasadirectorin2020.Likewise,Messrs.Black,Humphreys,Lohr,andSafferdidnotreceiveanycompensationfortheirservicesasadirector.NordidMr.GaryParr,whoresignedfromtheBoardeffectiveDecember10,2020.AlldirectorsarereimbursedfortravelandotherrelatedexpensesincurredwhileattendingBoardmeetings.

Senior Management Compensation

During 2020, the members of senior management identified in Item 6A (including Mr. Cloutier) received approximately $13.8 million in aggregatecompensation. This is comprised of: (i) base salary of approximately $5.2 million, (ii) discretionary bonuses, which include annual bonuses paid in 2021 forserviceduring2020ofapproximately$7.7million;and(iii)pension,retirement,andotherbenefitsofapproximately$0.9million.

TherearecurrentlynoequitycompensationplansunderwhichequitysecuritiesoftheCompanyareauthorizedforissuance.

C. Board Practices

TheBoardcurrentlyconsistsoftendirectors(seeItem6Aabove).ThecurrentdirectorsontheBoardhavebeenelectedtoserveuntilthenextAnnualGeneralMeeting of the Company or until their appointment is terminated in accordance with the Bye-Laws of the Company. On December 10, 2020, the CompanyannouncedthatMr.Irelandwillnotstandforre-electionattheCompany’s2021AnnualGeneralMeetingandthatitisanticipatedthatMr.LightowlerwillsucceedMr.IrelandasChairoftheAuditCommitteefollowingthe2021AnnualGeneralMeeting.

There are no service contracts between the Company and any of the Company’s non-executive directors providing for benefits upon termination of theirservice.

Audit Committee

TheAuditCommitteeiscomprisedofMessrs.Ireland(Chair)andBeer.Asnotedabove,itisanticipatedthatMr.Irelandwillnotstandforre-electionattheCompany’s2021AnnualGeneralMeetingandthatMr.LightowlerwillsucceedMr.IrelandasChairoftheAuditCommitteefollowingthe2021AnnualGeneralMeeting.PursuanttoitsCharter,theAuditCommitteehasgeneralresponsibilitytoassisttheBoardinitsoversightof:(i)theintegrityoftheCompany’sfinancialstatements, including the accounting and financial reporting process of the Company and audits of the Company’s financial statements; (ii) the Company’scompliancewithlegalandregulatoryrequirements;(iii)theexternalindependentauditors’qualifications,performanceandindependence;and(iv)theperformanceof the Company’s internal audit functions. Among other things, the Audit Committee annually reviews the qualifications of the independent auditors, makesrecommendationstotheBoardastotheirselectionandreviewstheplan,feesandresultsoftheiraudit.

TheBoarddeterminedthateachofthemembersoftheAuditCommitteeaswellasMr.LightowlerarefinanciallyliterateassuchtermisdefinedbyapplicableNYSEandSECrequirements. Inaddition,theBoardhasdeterminedthatMr.IrelandandMr.Lightowlereachqualifyasan“auditcommitteefinancialexpert”pursuanttotherulesandregulationsoftheSEC.

Other Committees

TheBoardcurrentlyhasaRiskCommitteeaswellasaConflictsCommittee.See“Item4B-BusinessOverview-RiskManagement”formoreinformationregardingthesecommittees.

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D. Employees

AsatDecember31,2020,weemployed907personsinthefollowingcountries:Country As at December 31, 2020 As at December 31, 2019 December 31, 2018UnitedKingdom 448 461 611UnitedStates 366 406 429Bermuda 49 48 45Switzerland 19 18 21Singapore 22 22 26Ireland — — 9UnitedArabEmirates — 5 7Australia 3 3 3Total 907 963 1,151

The decrease in the number of employees in 2020 compared to 2019 was primarily driven by the continued implementation of our expense savingsinitiatives,outsourcingstrategyaswellasthesaleofourSuretyinsuranceoperations.Webelievethatrelationswithouremployees,noneofwhicharesubjecttocollectivebargainingagreements,aregood.

E. Share Ownership

Notapplicable.100%oftheCompany’sordinarysharesareownedbyParentandtherearenootherordinarysharesorclassesofordinarysharesissuedandnoshare-basedcompensationplansasatDecember31,2020.

Item 7. Major Shareholders and Related Party Transactions

A. Major Shareholders

AsmorefullydescribedinItem18,Note1toourconsolidatedfinancialstatements,“History,OrganizationandBusinessCombination,”followingtheMerger,Parentowns100%oftheCompany’sissuedandoutstandingordinaryshares.ParentisanaffiliateofcertaininvestmentfundsmanagedbyaffiliatesofApollo.

B. Related Party Transactions

Relationships and Related Party Transactions with Apollo or its Affiliates

Parent, an affiliate of certain investment funds managed by Apollo, owns all of the Company’s ordinary shares. Additionally, certain of our directors areemployeesofApolloanditsaffiliates.Namely,Messrs.Black,Humphreys,Lohr,andSafferareemployeesofApollo.

Foradisclosureofotherrelatedpartytransactions,refertoItem18,Note19ofourconsolidatedfinancialaccounts,“RelatedPartyTransactions.”

C. Interests of Experts and Counsel

Notapplicable.

Item 8. Financial Information

A. Consolidated Statements and Other Financial Information

ReferenceismadetoItem18ofthisreport,fortheconsolidatedfinancialstatementsandreportsoftheCompanyandtheNotesthereto,aswellastheschedulestotheconsolidatedfinancialstatements.

B. Significant Changes

RefertoItem18,Note24totheconsolidatedfinancialstatements“SubsequentEvents”foradisclosureofeventssubsequenttothebalancesheetdate.

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Item 9. The Offer and Listing

A.Offer and Listing Details

As a result of the Merger, all of the Company’s publicly traded ordinary shares were automatically canceled. The ordinary shares of the Company ceasedtradingontheNYSEpriortotheopeningoftradingonFebruary15,2019.TheCompany’spreferencesharesanddepositarysharescontinuetobelistedontheNYSEunderthefollowingsymbols:AHLPRC,AHLPRDandAHLPRE.Foradditionaldetail,refertoItem18,Note12,“CapitalStructure”inItem18ofthisreport.

B.Plan of Distribution

Notapplicable.

C. Markets

The Company’s preference shares and the depositary shares are listed and traded on the NYSE. The 5.950%Fixed-to-Floating Perpetual Non-CumulativePreferenceShares(NYSE:AHLPRC)begantradingonMay7,2013.The5.625%PerpetualNon-CumulativePreferenceShares(NYSE:AHLPRD)begantradingonSeptember21,2016,andthedepositaryshares(NYSE:AHLPRE),eachrepresentinga1/1000 interestinashareoftheCompany’s5.625%PerpetualNon-CumulativePreferenceSharesbegantradingonAugust13,2019.

D.Selling Shareholders

Notapplicable.

E.Dilution

Notapplicable.

F.Expenses of the Issue

Notapplicable.

Item 10. Additional Information

A.Share Capital

Notapplicable.

B.Memorandum and Articles of Association

Theinformationrequiredbythis section, includingasummaryofcertain keyprovisionsof theCompany’s MemorandumofAssociationandAmendedandRestated Bye-laws were included in our Form S-3 (Registration No. 333-231937) filed with the SEC on June 4, 2019 (the “Registration Statement”), whichsummaryisincorporatedhereinbyreference.OurMemorandumofAssociationwasfiledasExhibit3.1toaForm6-KfiledwiththeSEConJuly29,2019,whichForm 6-K was incorporated by reference into the Registration Statement. Our Amended and Restated Bye-laws were filed as Exhibit 3.4 to the RegistrationStatement.

C. Material Contracts

Merger Agreement:

OnAugust28,2018,theCompanyenteredintotheMergerAgreementwithParentandMergerSub.PursuanttotheMergerAgreement,ParentacquiredalloftheoutstandingordinarysharesoftheCompanyforanall-cashconsiderationof$42.75pershare.ThetransactionwascompletedbyamergerofMergerSubwithand into the Company, with the Company continuing as the surviving entity. Pursuant to the terms of the Merger Agreement, (i) each issued and outstandingordinaryshare,parvalue$0.015144558perordinaryshare,oftheCompany(each,an“OrdinaryShare”)(otherthananyOrdinarySharesthatareownedbytheCompanyastreasuryshares,ownedbyanysubsidiaryoftheCompanyorownedbyParentorMergerSuboranysubsidiarythereof)wasautomaticallycanceledandconvertedintotherighttoreceive$42.75incash,withoutinterestandlessanyrequiredtaxwithholdingsand(ii)eachissuedandoutstanding5.95%Fixed-to-FloatingRatePerpetualNon-CumulativePreferenceShareoftheCompanyandeachissuedandoutstanding5.625%PerpetualNon-CumulativePreferenceShareof the Company remained issued and outstanding as a preference share of the Surviving Company, in each case, entitled to the same dividend and all otherpreferencesandprivileges,rights,qualifications,limitations,andrestrictionssetforthintheapplicablecertificateofdesignation.

The Merger was approved by the Company’s shareholders on December 10, 2018. On February 15, 2019, the Company announced completion of theacquisitionfollowingregulatoryclearanceandcompletionofothercustomaryclosingconditions.

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Management Consulting Agreement with Apollo Management

OnMarch28,2019,theCompanyenteredintoaManagementConsultingAgreement,datedMarch28,2019(the“ManagementConsultingAgreement”),byand between the Company and Apollo Management Holdings, L.P., a Delaware limited partnership (“Apollo Management”). Pursuant to the ManagementConsultingAgreement,ApolloManagementwillprovidetheAspenGroupwithmanagementconsultingandadvisoryservicesrelatedtothebusinessandaffairsoftheAspenGroupandAspenwillpaytoApolloManagementinconsiderationforitsservicesundertheAgreementanannualmanagementconsultingfeeequaltothegreaterof(i)1%oftheconsolidatednetincomeoftheAspenGroupfortheapplicablefiscalyear,and(ii)$5million.

FormoreinformationabouttheManagementConsultingAgreement,refertoNote19,“RelatedPartyTransactions”inItem18ofthisreport.

Information Technology Outsourcing Agreement:

OnAugust31,2018,AspenInsuranceUKServicesLimited,AspenInsuranceU.S.ServicesInc.andAspenBermudaenteredintoanOutsourcingAgreement(the “Original IT Outsourcing Agreement”) with Cognizant Worldwide Limited, a company registered in England (“Cognizant”). Pursuant to the Original ITOutsourcing Agreement, Cognizant provided the Company with information technology services to enable us to deliver greater operating effectiveness andefficiencies. TheOriginalITOutsourcingAgreementbecameeffectiveAugust31,2018andhadaninitial termperiodoffiveyearsfromOctober1,2018.TheCompany had the right to extend the IT Outsourcing Agreement for an additional two year term. In 2020, the Company paid Cognizant approximately $16.2millionforservicesrenderedundertheOriginalITOutsourcingAgreement.

On December 31, 2020, Aspen Insurance UK Services Limited, Aspen Insurance U.S. Services Inc. and Aspen Bermuda entered into a new OutsourcingAgreement(the“ITOutsourcingAgreement”)withCognizant,whichreplacedandsupersededtheOriginalITOutsourcingAgreementandsignificantlyreducedthe information technology services provided thereunder. The IT Outsourcing Agreement became effective December 31, 2020 and has an initial termof fouryears.TheCompanyhastherighttoextendtheITOutsourcingAgreementforanadditionaltwoyearterm.

TheITOutsourcingAgreementcontainscustomaryrepresentationsandwarrantiesandindemnity,terminationanddefaultprovisions.WemayterminatetheITOutsourcingAgreementforanyreasonbyprovidingninetydays’priorwrittennotice.Inaddition,wemayterminatetheITOutsourcingAgreementasaresultof,amongotherthings,amaterialbreachifnotcuredwithinaspecifiedtime,insolvency,persistentbreaches,failuretomeetkeymilestones,materialadversechangeasdefinedintheITOutsourcingAgreementorparticularcircumstancesconstitutingachangeincontrol.

Business Process Outsourcing Agreement:

OnApril20,2018,AspenInsuranceUKServicesLimited,AspenInsuranceU.S.Services,Inc.andAspenBermudaenteredintoanOutsourcingAgreement(the “BPO Outsourcing Agreement”) with Genpact International, Inc., a company incorporated in Delaware, United States (“Genpact”). Pursuant to theAgreement,Genpactwillprovideuswitharangeofoperationalbusinessprocesses,primarilyfromtheiroffshoreservicecenterinGurgaon,India,toenableustodeliver greater operatingeffectiveness andefficiencies. TheBPOOutsourcingAgreementbecameeffectiveApril 1, 2018andhasaninitial termperiodoffiveyears.WehavetherighttoextendtheBPOOutsourcingAgreementforthreeadditionaloneyearterms.

UnderthetermsoftheBPOOutsourcingAgreement,GenpactwillprovidesupportfunctionservicestotheCompany.TheBPOOutsourcingAgreementhasminimumservicelevelsthatGenpactmustmeetorexceed.ThecompensationstructureundertheBPOOutsourcingAgreementincludesacombinationoffixedandvariablefeeswhichmayfluctuate,assetforthintheBPOOutsourcingAgreement,basedonouractualuseofGenpact’sservices.In2020,theCompanypaidGenpactapproximately$10.5millionforservicesrenderedundertheBPOOutsourcingAgreement.Additionally,wehavetherighttoperiodicallycomparethechargesundertheBPOOutsourcingAgreementtothemarketpricesforcomparableservices.

TheBPOOutsourcingAgreementcontainscustomaryrepresentationsandwarrantiesandindemnity,terminationanddefaultprovisions.WemayterminatetheBPOOutsourcingAgreementforanyreasonbyprovidingninety(90)days’priorwrittennoticeandpayingafeerangingfrom$125,000to$3.5million,dependingonthecircumstances.Inaddition,wemayterminatetheBPOOutsourcingAgreementasaresultof,amongotherthings,amaterialbreachifnotcuredwithinaspecifiedtime,persistentbreaches,insolvency,changeofcontrol,failuretomeetkeymilestonesormaterialadversechangeasdefinedintheBPOOutsourcingAgreement.

OnJune29,2018,weenteredintoanovationagreement,effectiveApril1,2018(the“NovationAgreement”),withGenpactU.S.andGenpact(UK)Limited,acompanyregisteredinEnglandandWales(“GenpactU.K.”).UnderthetermsoftheNovationAgreement,therightsandobligationsofGenpactU.S.undertheBPOOutsourcingAgreement,weretransferredtoandundertakenbyGenpactU.K.

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D.Exchange Controls

SecuritiesmaybeofferedorsoldinBermudaonlyincompliancewiththeprovisionsoftheInvestmentBusinessActof2003,andtheExchangeControlAct1972,andrelatedregulationsofBermudathatregulatethesaleofsecuritiesinBermuda.Inaddition,specificpermissionisrequiredfromtheBMA,pursuanttotheprovisionsoftheExchangeControlAct1972andrelatedregulations,forallissuancesandtransfersofsecuritiesofBermudacompanies,otherthanincaseswheretheBMAhasgrantedageneralpermission.TheBMAinitspolicydatedJune1,2005providesthatwhereanyequitysecuritiesofaBermudacompanyarelistedon an appointed stock exchange (the NYSE is such an exchange), general permission is given for the issue and subsequent transfer of any securities of thecompanyfromand/ortoanon-residentofBermuda,foraslongasanyequitysecuritiesofthecompanyremainsolisted.

E.Taxation

Bermuda Taxation

Currently,thereisnoBermudaincome,corporateorprofitstaxorwithholdingtax,capitalgainstaxorcapitaltransfertax,estateorinheritancetaxpayablebyholdersofourshares,otherthanshareholdersordinarilyresidentinBermuda,ifany.

United States Taxation

Thefollowingsummarysets forth thematerial U.S. federal incometaxconsiderations relatedto thepurchase, ownershipanddispositionof theCompany’spreference shares, including the preference shares represented by the depositary shares (collectively, the “Preference Shares”). Unless otherwise stated, thissummarydealsonlywithshareholderswhoareU.S.Persons(asdefinedbelow)whopurchasePreferenceShares.Thefollowingdiscussionisonlyadiscussionofthe material U.S. federal income tax matters as described herein and does not purport to address all of the U.S. federal income tax consequences that may berelevant to a particular shareholder in light of suchshareholder’s specific circumstances. In addition, the followingsummary does not address the U.S. federalincome tax consequences that may be relevant to special classes of shareholders, such as financial institutions, insurance companies, regulated investmentcompanies, real estate investment trusts, financial asset securitization investment trusts, dealers or traders in securities or currencies, tax-exempt organizations,U.S.expatriates,partnershipsorotherpass-throughentities(orinvestorsinsuchentities),personswhosefunctionalcurrencyisnottheU.S.dollar,personssubjectto the alternative minimum tax, accrual basis taxpayers subject to special tax accounting rules under Section 451(b) of the Code, persons who are 10% U.S.Shareholders,orpersonswhoholdtheirsharesaspartofahedgingorconversiontransactionoraspartofashort-saleorstraddle,whomaybesubjecttospecialrules or treatment under the Code. This discussion is based upon the Code, the Treasury Regulations promulgated thereunder and any relevant administrativerulingsorpronouncementsorjudicialdecisions,allasineffectonthedatehereofandascurrentlyinterpreted,anddoesnottakeintoaccountpossiblechangesinsuch tax laws or interpretations thereof, which may apply retroactively. This discussion does not include any description of the tax laws of any state or localgovernments within the United States or of any non-U.S. government. Persons owning or considering making an investment in the Preference Shares shouldconsulttheirowntaxadvisorsconcerningtheapplicationoftheU.S.federaltaxlawstotheirparticularsituationsaswellasanytaxconsequencesarisingunderthelawsofanystate,localorforeigntaxingjurisdictionpriortomakingsuchinvestment.

Ifapartnership(orotherentitytreatedasapartnershipforU.S.federalincometaxpurposes)holdsthePreferenceShares,thetaxtreatmentofthepartnerswillgenerallydependonthestatusofthepartnerandtheactivitiesofthepartnership.Ifyouareapartnerofapartnershipowningourshares,youshouldconsultyourtaxadvisor.

Forpurposesofthisdiscussion,theterm“U.S.Person”means:(i)anindividualcitizenorresidentoftheUnitedStates,(ii)apartnershiporcorporationcreatedinororganizedunderthelawsoftheUnitedStates,ororganizedunderthelawsofanypoliticalsubdivisionthereof,(iii)anestatetheincomeofwhichissubjecttoU.S. federal incometaxation regardless of its source, (iv) a trust if either (x) a court within the United States is able to exercise primary supervision over theadministrationofsuchtrustandoneormoreU.S.Personshavetheauthoritytocontrolallsubstantialdecisionsofsuchtrustor(y)thetrusthasavalidelectionineffecttobetreatedasaU.S.PersonforU.S.federalincometaxpurposesor(v)anyotherpersonorentitythatistreatedforU.S.federalincometaxpurposesasifitwereoneoftheforegoing.

Treatment of Depositary Shares. A holder of depositary shares evidenced by depositary receipts generally should be treated for U.S. federal income taxpurposesastheownerofsuchholder’sproportionateinterestinthePreferenceSharesheldbythedepositary(oritscustodian)thatarerepresentedandevidencedbysuchdepositaryreceiptsandthediscussionhereinassumessuchtreatment.Accordingly,anydepositorwithdrawalofthePreferenceSharesbyaU.S.PersoninexchangefordepositarysharesgenerallywillnotresultintherealizationofgainorlosstosuchU.S.PersonforU.S.federalincometaxpurposes.

Taxation of Distributions. Subject to the discussions belowrelating to the potential application of the CFC, RPII andPFICrules, and the discussion belowrelatingtoredemptionsofPreferenceShares,cashdistributions,ifany,madewithrespecttothe

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PreferenceShareswill constitutedividendsforU.S.federalincometaxpurposestotheextentpaidoutofcurrentoraccumulatedearningsandprofitsofAspenHoldings (as computed using U.S. tax principles). To the extent such distributions exceed Aspen Holdings’ earnings and profits, they will be treated first as areturnoftheshareholder’sbasisintheirsharestotheextentthereof,andthenasgainfromthesaleofacapitalasset.If, asexpected,AspenHoldingsdoesnotcomputeitsearningsandprofitsunderU.S.taxprinciples,alldistributionsgenerallywillbetreatedasdividendsforU.S.federalincometaxpurposes.Dividendspaid by us to U.S. Persons who are corporations generally will not be eligible for a dividends received deduction. We believe dividends paid by us on ourPreferenceSharestonon-corporateholdersshouldbeeligibleforreducedratesoftaxationas“qualifieddividendincome”if,asisintended,thePreferenceSharesremainlistedontheNYSEandprovidedcertainrequirements,includingstockholdingperiodrequirements,aresatisfied.Qualifieddividendincomeissubjecttotaxatlong-termcapitalgainsratesratherthanthehigherratesapplicabletoordinaryincome.

Dividendsthatexceedcertainthresholdsinrelationtoashareholder’staxbasisinthePreferenceSharescouldbecharacterizedasan“extraordinarydividend”undertheCode.Anon-corporate holderofourPreferenceSharesthat receivesanextraordinarydividendwill berequiredtotreat anylossesonthesaleofourPreferenceSharesaslong-termcapitallossestotheextentoftheextraordinarydividendssuchshareholderreceivesthataretreatedasqualifieddividendincome.

Classification of Aspen Holdings or Its Non-U.S. Subsidiaries as CFCs.Each10%U.S.Shareholderofanon-U.S.corporationthatisaCFCatanytimeduringataxableyearmustincludeinitsgrossincomeforU.S.federalincometaxpurposesitsproratashareoftheCFC’s“subpartFincome”and“testedincome”(withvariousadjustments)withrespecttoanysharesthatsuch10%U.S.Shareholderownsinsuchnon-U.S.corporation(directlyorindirectlythroughcertainentities)on the last day in the non-U.S. corporation’s taxable year on which it is a CFC, even if the subpart F income or tested income is not distributed. “Subpart Fincome” of a CFCgenerally includes “foreign personal holding company income” (such as interest, dividends and other types of passive income), as well asinsuranceandreinsuranceincome(includingunderwritingandinvestmentincome), andtestedincomeisgenerallyanyincomeoftheCFCotherthansubpartFincomeandcertainothercategoriesofincome.AnentitytreatedasaforeigncorporationforU.S.federalincometaxpurposesisgenerallyconsideredaCFCif“10%U.S.Shareholders”own(directly,indirectlythroughnon-U.S.entitiesorconstructively)morethan50%ofthetotalcombinedvotingpowerofallclassesofstockof that non-U.S. corporationor morethan50%ofthetotal valueof all stockof that non-U.S. corporation. However, for purposesof takingintoaccountinsuranceincome,these50%thresholdsaregenerallyreducedto25%.

Wecurrently believethat AspenHoldingsis not a CFC,duetotheapparent dispersionof our share ownership. However, our shares maynot beas widelydispersedaswebelieve, andtheapplicationoftheindirect andconstructiveownershiprulesdependsuponfacts regardingourdirect andindirect shareholders,aboutwhichwehavelimitedinformation.Accordingly,noassurancecanbeprovidedthatAspenHoldingswillnotbeaCFC.Further,regardlessofwhetherAspenHoldingsisaCFC,mostorallofournon-U.S.subsidiariesaregenerallytreatedasCFCsbyreasonofcertainchangesintheconstructiveownershiprulesunderthe2017ActthatresultedinourU.S.subsidiariesgenerallybeingtreatedasconstructivelyowningthestockofournon-U.S.subsidiaries.Accordingly,any10%U.S.ShareholdersofAspenHoldingsmayberequiredtoincludeingrossincomeforU.S.federalincometaxpurposesforeachtaxableyeartheirproratasharesofalloraportionofthesubpartFandtestedincomegeneratedbyournon-U.S.companies,regardlessofwhetheranydistributionsaremadetothem.Anysuch10%U.S.Shareholdersshouldconsulttheirowntaxadvisorsregardingtheapplicationoftheserulestothem.

The RPII CFC Provisions.Ingeneral,ifanon-U.S.corporationisaRPIICFCatanytimeduringataxableyear,aU.S.RPIIShareholdermustincludeinitsgrossincomeforU.S.federalincometaxpurposesitsproratashareofthenon-U.S.corporation’sRPIIwithrespecttoanysharesthatsuchU.S.RPIIShareholderowns(directlyorindirectlythroughcertainentities)onthelastdayinthenon-U.S.corporation’staxableyear,eveniftheRPIIisnotdistributed.Further,aU.S.RPIIShareholder’sproratashareofanyRPIIisdeterminedasifallRPIIforthetaxableyearweredistributedproportionatelyonlytoU.S.RPIIShareholdersonthatdate.Inaddition,aU.S.RPIIShareholderisrequiredtocomplywithcertainreportingrequirements, regardlessofthenumberofsharesownedbytheU.S.RPIIShareholder.

Forthesepurposes,RPIIisany“insuranceincome”(asdescribedbelow)attributabletopoliciesofinsuranceorreinsurancewithrespecttowhichtheperson(directlyorindirectly)insuredisaU.S.RPIIshareholderora“relatedperson”(asdefinedbelow)tosuchU.S.RPIIshareholder.Ingeneral,andsubjecttocertainlimitations,“insuranceincome”isincome(includingpremiumandinvestmentincome)attributabletotheissuingofanyinsuranceorreinsurancecontractwhichwouldbetaxedundertheportionsoftheCoderelatingtoinsurancecompaniesiftheincomeweretheincomeofaU.S.domesticinsurancecompany.Generally,theterm“relatedperson”forthispurposemeanssomeonewhocontrolsoriscontrolledbytheU.S.RPIIShareholderorsomeonewhoiscontrolledbythesamepersonorpersonswhocontroltheU.S.RPIIShareholder.Controlgenerallyismeasuredbyagreaterthan50%ownershipinterest,applyingcertainconstructiveownershipprinciples.However,theRPIIrulesgenerallydonotapplywithrespecttoanon-U.S.corporationifeither(i)atalltimesduringitstaxableyearlessthan20%ofthetotalcombinedvotingpowerofallclassesofstockofthecorporationentitledtovoteandlessthan20%ofthetotalvalueofthecorporationisowned(directlyorindirectly)bypersonswhoare(directlyorindirectly)insuredunderanypolicyofinsuranceorreinsuranceissuedbythecorporationorwhoarerelatedpersonstoanysuchperson(the“ownership

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exception”),or(ii)theRPII(determinedonagrossbasis)ofthecorporationforthetaxableyearislessthan20%ofitsgrossinsuranceincomeforthetaxableyear(the“deminimisexception”).

Webelievethateachournon-U.S.OperatingSubsidiariesandeachofSilverton,PeregrineandAPJJerseyisaRPIICFC.Nonetheless,weexpectthateachsuchcompanywill qualify for oneor bothof theownershipexceptionandthedeminimis exceptionin thecurrent taxable year andfor theforeseeable future.However,noassurancescanbeprovidedthatanyofourcompanieswillsatisfyeitherexception.

ComputationofRPII.InordertodeterminehowmuchRPII,ifany,anon-U.S.insurancesubsidiaryhasearnedineachtaxableyear,ournon-U.S.insurancesubsidiaries may obtain and rely upon information from their insureds and reinsureds to determine whether any of the insureds, reinsureds or persons relatedthereto own (directly or indirectly through non-U.S. entities) shares of Aspen Holdings and are U.S. Persons. Aspen Holdings may not be able to determinewhetheranyoftheunderlyingdirectorindirectinsuredstowhichournon-U.S.insurancesubsidiariesprovideinsuranceorreinsuranceareshareholdersorrelatedpersonstosuchshareholders.Consequently,AspenHoldingsmaynotbeabletodetermineaccuratelythegrossamountofRPIIearnedbyeachofournon-U.S.insurancesubsidiariesinagiventaxableyear.ForanyyearinwhichthespecialRPIICFCinclusionrulesapply,AspenHoldingsmayalsoseekinformationfromitsshareholdersastowhetherbeneficialownersofsharesattheendoftheyearareU.S.PersonssothattheRPIImaybedeterminedandapportionedamongsuchpersons;totheextentAspenHoldingsisunabletodeterminewhetherabeneficialownerofsharesisaU.S.Person,AspenHoldingsmayassumethatsuchownerisnotaU.S.Person,therebyincreasingthepershareRPIIamountforallknownU.S.RPIIShareholders.

Basis Adjustments.AU.S.RPIIShareholder’staxbasisinitsshareswillbeincreasedbytheamountofanyRPIIthattheshareholderincludesinincome.TheU.S. RPII Shareholder may exclude from income the amount of any distributions by Aspen Holdings out of previously taxed RPII income. The U.S. RPIIshareholder’staxbasisinitsshareswillbereducedbytheamountofsuchdistributionsthatareexcludedfromincome.

Uncertainty as to Application of RPII Provisions.The RPII provisions have never been interpreted by the courts, and regulations interpreting the RPIIprovisionsexistonlyinproposedform.Itisnotcertainwhethertheseregulationswillbeadoptedintheirproposedformorwhatchangesorclarificationsmightultimatelybemadetheretoorwhetheranysuchchanges,aswellasanyinterpretationorapplicationoftheRPIIprovisionsbytheIRS,thecourtsorotherwise,mighthaveretroactiveeffect.TheU.S.TreasuryDepartmenthasauthoritytoimpose,amongotherthings,additionalreportingrequirementswithrespecttoRPII.Accordingly, the meaning of the RPII provisions and the application thereof to us is uncertain. Further, the applicability of the ownership and de minimisexceptions and the RPII rules more generally depends upon facts regarding our direct and indirect shareholders and insureds, about which we have limitedinformation. Accordingly, noassurancescanbeprovidedthatanyofourcompanieswill satisfyeitherexception. Moreover, totheextenttheexceptionsdonotapply, wemaybeunabletocorrectly determinetheamountofRPIIthat anyU.S.RPIIShareholder is requiredtotakeintoaccount. Anyprospectiveinvestorsconsideringaninvestmentinoursharesshouldconsulttheirtaxadvisorsastotheeffectsoftheseuncertainties.

Information Reporting.Undercertaincircumstances,U.S.Personsowningstockinanon-U.S.corporationarerequiredtofileIRSForm5471withtheirU.S.federalincometaxreturns.Generally,informationreportingonIRSForm5471isrequiredby(i)apersonwhoistreatedasaU.S.RPIIShareholder,(ii)a10%U.S.Shareholderofanon-U.S.corporationthatisaCFCatanytimeduringthetaxableyearandwhoownedthestockonthelastdayofthatyearonwhichitwasaCFCand(iii) undercertaincircumstances, aU.S.Personwhoacquiresstockinanon-U.S.corporationandasaresultthereofowns10%ormoreofthevotingpowerorvalueofsuchnon-U.S.corporation,whetherornotsuchnon-U.S.corporationisaCFC.AspenHoldingswill,uponrequest,providetoallU.S.PersonsregisteredasshareholdersofitssharestherelevantinformationnecessarytocompleteForm5471intheeventAspenHoldingsdeterminesthisisnecessary.FailuretofileIRSForm5471mayresultinpenalties.

Tax-Exempt Shareholders.AU.S.tax-exemptorganizationgenerallywillrecognizeunrelatedbusinesstaxableincomeiftheorganizationisrequiredtoincludein gross income any of our insurance income under the CFCrules described above (including the RPII provisions). Prospective investors that are tax exemptentitiesareurgedtoconsulttheirtaxadvisorsastothepotentialimpactoftheunrelatedbusinesstaxableincomeprovisionsoftheCode.Atax-exemptorganizationthatistreatedasa10%U.S.ShareholderoraU.S.RPIIShareholderalsomustfileIRSForm5471inthecircumstancesdescribedabove.

Redemption of Preference Shares. AredemptionofthePreferenceShareswillbetreatedunderSection302oftheCodeasadistributionwithrespecttoourshares,unlesstheredemptionsatisfiesoneofthetestssetforthinSection302(b)oftheCodeenablingtheredemptiontobetreatedasadisposition(asdiscussedbelow),subjecttothediscussionhereinrelatingtothepotentialapplicationoftheCFC,RPIIandPFICrules.UndertherelevantCodeSection302(b)tests,theredemptiongenerallywillbetreatedasasaleorexchangeonlyifit(1)issubstantiallydisproportionate,(2)constitutesacompleteterminationoftheholder’sstockinterestinusor(3)is“notessentiallyequivalenttoadividend.”Indeterminingwhetheranyofthesetestsaremet,sharesconsideredtobeownedbytheholderbyreasonofcertainconstructiveownershiprulessetforthintheCode,as

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wellassharesactuallyowned,mustgenerallybetakenintoaccount.ItmaybemoredifficultforaU.S.Personwhoowns,actuallyorconstructivelybyoperationoftheattributionrules,anyofourothersharestosatisfyanyoftheaboverequirements. ThedeterminationastowhetheranyofthealternativetestsofSection302(b)oftheCodeissatisfiedwithrespecttoaparticularholderofthePreferenceSharesdependsonthefactsandcircumstancesasofthetimethedeterminationismade.

Dispositions of Preference Shares.SubjecttothediscussionaboverelatingtoredemptionsandthediscussionsbelowrelatingtothepotentialapplicationoftheCodeSection1248andPFICrules,U.S.PersonsthatholdPreferenceSharesgenerallyshouldrecognizecapitalgainorlossforU.S.federalincometaxpurposesonthesale,exchange,redemptionorotherdispositionofthePreferenceSharesinthesamemannerasonthesale,exchange,redemptionorotherdispositionofanyothersharesheldascapitalassets.Iftheholdingperiodforthesesharesexceedsoneyear,undercurrentlawanygainwillbesubjecttotaxattheratesapplicabletolong-termcapital gain. Moreover, gain,if any,generallywill beU.S.sourcegainandgenerallywill constitute“passivecategoryincome”forforeigntaxcreditlimitationpurposes.

CodeSection1248providesthatifaU.S.Personsellsorexchangesstockinanon-U.S.corporationandsuchpersonowned,directly,indirectlythroughcertainnon-U.S.entitiesorconstructively,10%ormoreofthevotingpowerofthecorporationatanytimeduringthefive-yearperiodendingonthedateofdispositionwhenthecorporationwasaCFC,anygainfromthesaleorexchangeoftheshareswillbetreatedasadividendtotheextentoftheCFC’searningsandprofits(determinedunderU.S.federal incometaxprinciples)duringtheperiodthattheshareholderheldthesharesandwhilethecorporationwasaCFC(withcertainadjustments). A U.S. Person who owns or owned, directly, indirectly through certain non-U.S. entities or constructively, 10%or more of the voting power ofAspenHoldingsmaybesubjecttotheserulesifAspenHoldingsisorwastreatedasaCFC.

A10%U.S.ShareholdermayincertaincircumstancesberequiredtoreportadispositionofsharesofaCFCbyattachingIRSForm5471totheU.S.federalincometaxorinformationreturnthatitwouldnormallyfileforthetaxableyearinwhichthedispositionoccurs.Intheeventthisisdeterminednecessary,AspenHoldingswillprovidetherelevantinformationnecessarytocompletetheForm.

PursuanttotheRPIIprovisions,Section1248oftheCodealsogenerallyappliesifaU.S.PersondisposesofsharesinaRPIICFC(determinedwithoutregardtotheownershipordeminimisexceptions)thatwouldbetaxableasaninsurancecompanyundertheCodeifitwereaU.S.corporation,inwhichcaseanygainfromthedisposition generally will be treated as a dividendto the extent of the holder’s share of the corporation’s undistributed earnings andprofits that wereaccumulatedduringtheperiodthattheholderownedtheshares(whetherornotsuchearningsandprofitsareattributabletoRPII).Inaddition,suchaholderwillberequired to comply with certain reporting requirements, regardless of the number of shares ownedby the holder. Existing proposed regulations do not addresswhetherSection1248oftheCodewouldapplyifanon-U.S.corporationisnotaninsurancecompanybutthenon-U.S.corporationhasasubsidiarythatisaCFCandthat wouldbe taxedas an insurance companyif it were a domestic corporation. Webelieve that these rules should not applyto dispositions of our sharesbecause Aspen Holdings will not itself be directly engaged in the insurance business. We cannot be certain, however, that the IRS will not interpret the RPIIprovisions in a contrary manner or that the U.S. Treasury Department will not adopt regulations that provide that these rules will apply to dispositions ofPreferenceShares.ProspectiveinvestorsshouldconsulttheirtaxadvisorsregardingtheeffectsoftheserulesonadispositionofPreferenceShares.

Tax on Net Investment Income.AU.S.Personthatisanindividual,estateoratrustthatdoesnotfallintoaspecialclassoftruststhatisexemptfromsuchtax,willbesubjecttoa3.8%taxonthelesserof(1)theU.S.Person’s“netinvestmentincome”(or“undistributednetinvestmentincome”inthecaseofestatesandtrusts)fortherelevanttaxableyearand(2)theexcessoftheU.S.Person’smodifiedadjustedgrossincomeforthetaxableyearoveracertainthreshold(whichinthe case of an individual will be between $125,000 and $250,000, depending on the individual’s circumstances). A U.S. Person’s net investment income willgenerally include its dividend incomeand its net gains fromthe disposition of Preference Shares, unless such dividend incomeor net gains are derived in theordinarycourseoftheconductofatradeorbusiness(otherthanatradeorbusinessthatconsistsofcertainpassiveortradingactivities).UnlessaU.S.Personelectsotherwise or holds Preference Shares in connection with certain trades or businesses, the CFC and PFIC provisions generally will not apply for purposes ofdeterminingaU.S.Peron’snetinvestmentincomewithrespecttothePreferenceShares.

Passive Foreign Investment Companies.Ingeneral,anon-U.S.corporationwillbeaPFICduringagivenyearif(i)75%ormoreofitsgrossincomeconstitutes“passiveincome”(the“75%test”)or(ii)50%ormoreofitsassetsproduce(orareheldfortheproductionof)passiveincome(the“50%test”).Forthesepurposes,passive incomegenerally includes interest, dividends, annuities andother investment income. However, the PFICprovisions contain a look-throughrule underwhichanon-U.S.corporationthat directly or indirectly ownsat least 25%ofthevalueofthestockofanother corporationgenerally is treated, for purposesofdetermining whether it is a PFIC, as if it received directly its proportionate share of the income, and held its proportionate share of the assets, of the othercorporation (the “look-through rule”). In addition, pursuant to an insurance exception that was amendedby the 2017Act, (a) passive incomedoes not includeincomethataQICderivesintheactiveconductofaninsurancebusinessorincomeofaQDIC,and(b)passiveassetsdonotincludeassetsofaQICavailabletosatisfy

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liabilitiesoftheQICrelatedtoitsinsurancebusiness,iftheQICisengagedintheactiveconductofaninsurancebusiness,orassetsofaQDIC.

Generally, a non-U.S. corporation will be a QIC for a taxable year if it would be taxable as an insurance company if it were a U.S. corporation and itsapplicableinsuranceliabilitiesconstitutemorethan25%ofitstotalassetsforataxableyear.Further,underthe2021ProposedRegulations,aQICisinthe“activeconduct” of an insurance business only if it satisfies either a “factual requirements test” or an “active conduct percentage test.” The factual requirements testrequiresthattheofficersandemployeesoftheQICcarryoutsubstantialmanagerialandoperationalactivitiesonaregularandcontinuousbasiswithrespecttoitscorefunctionsandthattheyperformvirtuallyall oftheactivedecision-makingfunctionsrelevanttounderwritingfunctions. Theactiveconductpercentagetestgenerally requires that (i) thetotal costs incurredbytheQICwithrespect to its officers andemployees for services renderedwithrespect to its core functions(otherthaninvestmentactivities)equalorexceed50%ofthetotalcostsincurredbytheQICwithrespecttoitsofficersandemployeesandanyotherpersonorentities for services rendered with respect to its core functions (other than investment activities) and (ii) to the extent the QIC outsources any part of its corefunctionstounrelatedentities,officersandemployeesoftheQICwithexperienceandrelevantexpertisemustselectandsupervisethepersonthatperformstheoutsourcedfunctions,establishobjectivesforperformanceoftheoutsourcedfunctionsandprescriberigorousguidelinesrelatingtotheoutsourcedfunctionswhichareroutinelyevaluatedandupdated.Undercertainexceptions,however,aQICthathasnooronlyanominalnumberofemployeesorthatisavehiclethathastheeffect of securitizing or collateralizing insurance risks underwritten by other insurance or reinsurance companies or is an insurance linked securities fund thatinvestsinsecuritizationvehiclesgenerallyisdeemednotengagedintheactiveconductofaninsurancebusiness. Theofficersandemployeesofcertainrelatedentitiesgenerallymaybetakenintoaccountforthesepurposes,providedthattheQICexercisesregularoversightandsupervisionovertheservicesperformedbytherelatedentity’sofficersandemployees.The2021ProposedRegulationswillnotbeeffectiveunlessanduntiladoptedinfinalform,buttaxpayersmayrelyonthemfortaxableyearsbeginningafterDecember31,2017iftheyareconsistentlyfollowed.

Webelievethat,basedontheimplementationofourcurrentbusinessplanandtheapplicationoftheinsuranceexception,ournon-U.S.insurancesubsidiariesshould be considered QICsengaged in the active conduct of an insurance business under one or both of the “factual requirements test” or the “active conductpercentagetest,”ourU.S.insurancesubsidiariesshouldbeconsideredQDICsandnoneoftheincomeorassetsofsuchinsurancesubsidiariesshouldbetreatedaspassive.Asaresult,basedontheapplicationofthelook-throughrule,webelievethatAspenHoldingsshouldnotbecharacterizedasaPFICforthecurrentyearortheforeseeablefuture.However,becauseoflegaluncertaintieswithrespecttotheinterpretationofthePFICrulesandwhetherthe2021ProposedRegulationswillbeadoptedasfinalregulationsintheircurrentform,andfactualuncertaintieswithrespecttoourplannedoperations,thereisariskthatAspenHoldingswillbecharacterizedasaPFICinoneormoreyears.

IfAspenHoldingsischaracterizedasaPFICforanyyearduringwhichaU.S.PersonholdssharesofAspenHoldings,itgenerallywillcontinuetobetreatedasaPFICfortheyearsduringwhichsuchU.S.Personholdssuchshares.

If Aspen Holdings were characterized as a PFICduring a given year, each U.S. Person holding shares of Aspen Holdings generally would be subject to apenaltytaxatthetimeofthesaleatagainof,orreceiptofan“excessdistribution”withrespectto,theirshares,unlesssuchpersonisa10%U.S.ShareholdersubjecttotaxundertheCFCrulesorsuchpersonmadea“qualifiedelectingfund”electionor“mark-to-market”election(whichmark-to-marketelectionwouldgenerallyrequiretheshareholdertoincludeasordinaryincomeanyappreciationinthevalueofitssharesattheendofataxableyearandallowashareholdertodeductanydepreciationinthevalueofitsshares(uptotheamountofpriorgaininclusions)atthecloseofthetaxableyear).ItisuncertainthatAspenHoldingswould be able to provide its shareholders with the information necessary for a U.S. Person to make a “qualified electing fund” election. In addition, if AspenHoldingswereconsideredaPFIC,uponthedeathofanyU.S.individualowningshares,suchindividual’sheirsorestatewouldnotbeentitledtoa“step-up”inthebasisofthesharesthatmightotherwisebeavailableunderU.S.federalincometaxlaws.Ingeneral,ashareholderreceivesan“excessdistribution”iftheamountofthedistributionismorethan125%oftheaveragedistributionwithrespecttothesharesduringthethreeprecedingtaxableyears(orshorterperiodduringwhichthetaxpayerheldtheshares).Ingeneral,thepenaltytaxisequivalenttothetaxesthataredeemeddueduringtheperiodtheshareholderownedtheshares,computedbyassumingthattheexcessdistributionorgain(inthecaseofasale)withrespecttotheshareswasearnedinequalportionsandtaxableatthehighestapplicabletaxrateonordinaryincomethroughouttheshareholder’speriodofownership,andaninterestchargeforthefailuretopaysuchtaxesforpriorperiods.TheinterestchargeisequaltotheapplicablerateimposedonunderpaymentsofU.S.federalincometaxforsuchperiods.Inaddition,adistributionpaidbyAspenHoldingstoU.S.shareholdersthatischaracterizedasadividendandisnotcharacterizedasanexcessdistributionwouldnotbeeligibleforreducedratesoftaxasqualifieddividendincomeifAspenHoldingswereconsideredaPFICinthetaxableyearinwhichsuchdividendispaidorintheprecedingtaxableyear.AU.S.PersonthatisashareholderinaPFICmayalsobesubjecttoadditionalinformationreportingrequirements,includingthefilingofanIRSForm8621.

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U.S.investorsareurgedtoconsultwiththeirtaxadvisorsandtoconsidermakinga“protective”QEFelectionwithrespecttothePreferenceSharestopreservethepossibilityofmakingaretroactiveQEFelection.AU.S.PersonthatmakesaQEFelectionwithrespecttoaPFICiscurrentlytaxableonitsproratashareoftheordinaryearningsandnetcapital gainofsuchcompanyduringtheyearsit isaPFIC(atordinaryincomeandcapital gainrates, respectively), regardlessofwhetherornotdistributionswerereceived.Inaddition,anyofthePFIC’slossesforataxableyearwillnotbeavailabletoU.S.PersonsandmaynotbecarriedbackorforwardincomputingthePFIC’sordinaryearningsandnet capital gaininothertaxableyears. AU.S.Persongenerallyincreasesthebasis ofits PFICshares, and the basis of any other property of the U.S. Person by reason of which such U.S. Person is considered to indirectly own PFIC shares, by amountsincludedinsuchU.S.Person’sgrossincomepursuanttotheQEFelection.Therefore,anelectingU.S.PersonwillgenerallyincreasethebasisofitsPreferenceSharesbyamountsincludedintheU.S.Person’sgrossincomepursuanttotheQEFelection.DistributionsofincomethathadpreviouslybeentaxedpursuanttotheQEFelectionwill result inacorrespondingreductionofbasis inthePreferenceSharesandwill not betaxedagainasadistributiontotheU.S.Person.AU.S.PersonholdingPreferenceShareswillgenerallyberequiredtofileanIRSForm8621(whichisaformthatisrequiredtobefiledbyholdersofequityinaPFIC)for each tax year that it holds Preference Shares and we are characterized as a PFIC, regardless of whether such U.S. Person has a QEF election in effect orreceivesanexcessdistribution.

IfAspenHoldingsisaPFICforanytaxableyear,aU.S.PersonwhoholdsourshareswouldbetreatedasowningaproportionateamountofthesharesofanyPFICsinwhichAspenHoldingsdirectly,orincertaincasesindirectly,ownsaninterest,andthePFICrulesdescribedabovegenerallywouldapplywithrespecttotheU.S.Person’sindirectownershipofsuchPFICs.

Foreign Tax Credit.IfU.S.Personsownamajorityofourshares,onlyaportionofthecurrentincomeinclusions,ifany,undertheCFC,RPIIandPFICrulesandofdividendspaidbyus(includinganygainfromthesaleofsharesthatistreatedasadividendunderSection1248oftheCode)will betreatedasforeignsourceincomeforpurposesofcomputingashareholder’sU.S.foreigntaxcreditlimitations.Wewillconsiderprovidingshareholderswithinformationregardingtheportionofsuchamountsconstitutingforeignsourceincometotheextentsuchinformationisreasonablyavailable.Itisalsolikelythatsubstantiallyallofthe“subpart F income,” RPII and dividends that are foreign source income will constitute “passive category income” for foreign tax credit limitation purposes.Additionally,testedincomewillconstituteaseparatebasketforforeigntaxcreditpurposes.Thus,itmaynotbepossibleformostshareholderstoutilizeexcessforeigntaxcreditstoreduceU.S.taxonsuchincome.

Information Reporting and Backup Withholding on Distributions and Disposition Proceeds.InformationreturnsmaybefiledwiththeIRSinconnectionwithdistributions on our shares and the proceeds from a sale or other disposition of our shares unless the holder of our shares establishes an exemption from theinformationreportingrules.AholderofsharesthatdoesnotestablishsuchanexemptionmaybesubjecttoU.S.backupwithholdingtaxonthesepaymentsiftheholderisnotacorporationorotherexemptrecipientorfailstoprovideitstaxpayeridentificationnumberorotherwisecomplywiththebackupwithholdingrules.TheamountofanybackupwithholdingfromapaymenttoaU.S.PersonwillbeallowedasacreditagainsttheU.S.Person’sU.S.federalincometaxliabilityandmayentitletheU.S.Persontoarefund,providedthattherequiredinformationisfurnishedtotheIRS.

UnderSection6038DoftheCode,certainU.S.PersonswhoareindividualsmayberequiredtoreportinformationrelatingtoaninterestinPreferenceShares,subject to certain exceptions (including an exception for Preference Shares held in accounts maintained by certain financial institutions). U.S. Persons shouldconsulttheirtaxadvisorsregardingthepotentialapplicationofthisandanyotherapplicableinformationreportingrequirementstotheirownershipofPreferenceShares.

Interpretation of the 2017 Act and Possible Changes in U.S. Tax Law.Itispossiblethatfutureregulatoryandjudicialinterpretationsofthe2017Act,aswellasanynewlegislationthatmaybeintroducedandenactedbythecurrentCongressorfutureCongresses,couldhaveanadverseimpactonusorholdersofPreferenceShares.Anysuchlegislationorinterpretationscouldhavearetroactiveeffect.

Additionally,theU.S.federalincometaxlawsandinterpretationsregardingwhetheracompanyisengagedinatradeorbusinesswithintheUnitedStatesorisa PFIC,or whether U.S. Personswouldberequiredtoincludeintheir grossincomethe“subpart Fincome,” “testedincome”or RPII of a CFC,are subject tochange,possiblyonaretroactivebasis.CertainoftheregulationsregardingtheapplicationofthePFICrulestoinsurancecompaniesandtheregulationsregardingRPIIarestillinproposedform.Newregulationsorpronouncementsinterpretingorclarifyingsuchrulesmaybeforthcoming.Wecannotbecertainif,whenorinwhatformsuchregulationsorpronouncementsmaybeprovidedandwhethersuchguidancewillhavearetroactiveeffect.

Common Reporting Standard.TheCommonReportingStandard(“CRS”)hasbeenintroducedasaninitiativebytheOECDandisimposedonmembersoftheEuropeanUnionbytheEuropeanDirectiveonAdministrativeCo-operation.SimilartothelegislationcommonlyknownastheForeignAccountTaxComplianceActintroducedbytheUnitedStates,theCRSrequires

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financialinstitutionswhicharesubjecttotherulestoreportcertainfinancialinformationinrespectofaccountholders.TheCRSbecameeffectiveasofJanuary1,2016andE.U.memberstatesgenerallybegantoexchangetherequiredinformationpursuanttotheCRSfromtheendofSeptember2017onwards.AnumberofotherjurisdictionsalsocommittedtojoiningtheCRSin2018.WeintendtooperateincompliancewithCRS.

F. Dividends and paying agents

Notapplicable.

G.Statement by Experts

Notapplicable.

H.Documents on Display

TheCompanymaintainsaninternetsiteatwww.aspen.cothatcontainsAnnualReportsonForm20-FandCurrentReportsonForm6-KfiledorfurnishedwiththeU.S.SecuritiesandExchangeCommission(“SEC”).ReportsandotherinformationwefilewiththeSECarealsoavailableontheinternetsitemaintainedbytheSECatwww.sec.gov.Registrationstatements,reportsandotherinformationwefilemaybereviewedandcopiedattheSEC’sPublicReferenceRoomat100FStreet,N.E.,Washington,DC20549.CopiesofthesedocumentsmayalsoberequesteduponpaymentofaduplicatingfeebywritingtotheSEC.

I.Subsidiary Information

Notapplicable.

Item 11. Quantitative and Qualitative Disclosures about Market Risk

Webelieveweareprincipallyexposedtothreetypesofmarketrisk:interestraterisk,foreigncurrencyriskandcreditrisk.

Interest rate risk. Our investment portfolio consists primarily of fixed income securities. Fluctuations in interest rates have a direct impact on the marketvaluationofthesesecurities. Accordingly,ourprimarymarketriskexposureistochangesininterestrates. Asinterestratesrise,themarketvalueofourfixed-incomeportfoliofallsandtheconverseisalsotrue.Wemanageinterestrateriskbymaintainingashorttomediumdurationtoreducetheeffectofinterestratechangesonbookvalue.OnJanuary16,2019,AspenBermudaenteredintoanumberofstandardfixedforfloatinginterestrateswapswithatotalnotionalamountof$3,138.0millionwhichwereduetomaturebetweenJanuary18,2021andJanuary18,2034,allofwhichhavesincebeenunwound.InSeptember2020,wedecidedtounwindourremaininginterestrateswappositions.AspenBermudaenteredintotheswapsintheordinarycourseofitsinvestmentactivitiestopartiallymitigateanynegativeimpactofrisesininterestratesonthemarketvalueofourfixedincomeportfolio.ForthetwelvemonthsendedDecember31,2020,therewasalossof$81.1million(December31,2019—$130.2million).

AsatDecember31,2020,noinitialandvariationmarginwaspostedtoaFuturesCommissionMerchantastheinterestrateswaphadbeenwoundupintheyear(December31,2019—$111.1million).AsatDecember31,2020,nonon-cashcollateralwastransferredtotheCompanybyitscounterparties(December31,2019—$Nil).TransfersofmarginarerecordedontheconsolidatedbalancesheetwithinDerivativesatFairValue,whiletransfersinrespectofnon-cashcollateralaredisclosedbutnotrecorded.AsatDecember31,2020,noamountwasrecordedintheconsolidatedbalancesheetforthepledgedassets.

AsatDecember31,2020,ourfixedincomeportfoliohadanapproximatedurationof2.7years.Thetablebelowdepictsinterestratechangescenariosandtheeffectonourinterestratesensitiveinvestedassets:

Effect of Changes in Interest Rates on Portfolio Given a Parallel Shift in the Yield CurveMovement in Rates in Basis Points -100 -50 0 50 100 ($ in millions, except percentages)MarketValue 5,779.7 5,702.6 5,625.4 5,548.2 5,471.1Gain/Loss 154.3 77.2 — (77.2) (154.3)PercentageofPortfolio 2.7% 1.4% — (1.4)% (2.7)%CorrespondingpercentageatDecember31,2019 3.0% 1.5% — (1.5)% (3.1)%

(1)Marketvalueincludesourfixedincomeportfolio,shortterminvestmentsandprivatelyheldinvestments.Foreign currency risk.OurreportingcurrencyistheU.S.Dollar.ThefunctionalcurrenciesofouroperationsareU.S.Dollars,BritishPounds,Euros,Swiss

Francs,AustralianDollars,CanadianDollarsandSingaporeanDollars.AsatDecember31,2020,approximately88.1%ofourcashandinvestmentswasheldinU.S.Dollars(2019—86.0%),

(1)

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approximately2.1%wereinBritishPounds(2019—4.8%)andapproximately9.8%wereincurrenciesotherthantheU.S.DollarandtheBritishPound(2019—9.2%).ForthetwelvemonthsendedDecember31,2020,14.7%ofourgrosspremiumswerewrittenincurrenciesotherthantheU.S.DollarandtheBritishPound(2019—15.9%)andweexpectthatasimilarproportionwillbewrittenincurrenciesotherthantheU.S.DollarandtheBritishPoundin2021.

Otherforeigncurrencyamountsareremeasuredtotheappropriatefunctionalcurrencyandtheresultingforeignexchangegainsorlossesarereflectedinthestatementofoperations.FunctionalcurrencyamountsofassetsandliabilitiesarethentranslatedintoU.S.Dollars.Theunrealizedgainorlossfromthistranslation,netoftax,isrecordedaspartofordinaryshareholders’equity.Thechangeinunrealizedforeigncurrencytranslationgainorlossduringtheyear,netoftax,isacomponent of comprehensive income. Both the remeasurement and translation are calculated using current exchange rates for the balance sheets and averageexchangeratesforthestatementofoperations.Wemayexperienceexchangelossestotheextentthatourforeigncurrencyexposureisnotproperlymanagedorotherwisehedgedwhichwouldinturnadverselyaffectourresultsofoperationsandfinancialcondition.Managementestimatesthata10%changeintheexchangeratebetweenBritishPoundsandU.S.DollarsasatDecember31,2020wouldhaveimpactedreportednetcomprehensiveincomebyapproximately$20.5million(2019—$9.2million).

Wewillcontinuetomanageourforeigncurrencyriskbyseekingtomatchourliabilitiesunderinsuranceandreinsurancepoliciesthatarepayableinforeigncurrencies with investments that are denominated in those currencies. This may involve the use of forward exchange contracts from time to time. A foreignexchange contract involves an obligation to purchase or sell a specified currency at a future date at a price set at the time of the contract. Foreign exchangecontracts will not eliminate fluctuations in the value of our assets and liabilities denominated in foreign currencies but rather allow us to establish a rate ofexchangeforafuturepointintime.

As at December 31, 2020, we held foreign exchange contracts that were not designated as hedging under ASC 815,“Derivatives and Hedging”with anaggregatenotionalvalueof$1,402.3million(2019—$1,696.3million).Theforeignexchangecontractsarerecordedasderivativesatfairvalueinthebalancesheetwithchangesrecordedasachangeinfairvalueofderivativesinthestatementofoperations.ForthetwelvemonthsendedDecember31,2020,theimpactofforeignexchangecontractsonnetincomewasagainof$16.0million(December31,2019—lossof$14.0million).

As at December 31, 2020, we held foreign exchange contracts that were designated as hedging under ASC815 with an aggregate notional value of $90.6million(2019—$85.5million).Theforeignexchangecontractsarerecordedasderivativesatfairvalueinthebalancesheetwiththeeffectiveportionrecordedinother comprehensive income and the ineffective portion recorded as a change in fair value of derivatives in the statement of operations. The contracts areconsideredtobeeffectiveandthemovementinothercomprehensiveincomerepresentingtheeffectiveportionwasagainof$0.3millionforthetwelvemonthsendedDecember31,2020(December31,2019—gainof$4.8million).

Astheforeignexchangecontractssettle,therealizedgainorlossisreclassifiedfromothercomprehensiveincomeintogeneral,administrationandcorporateexpensesofthestatementofoperationsandothercomprehensiveincome.ForthetwelvemonthsendedDecember31,2020,theamountrecognizedwithingeneral,administrationandcorporateexpensesforsettledforeignexchangecontractswasarealizedlossof$3.2million(December31,2019—gainof$0.9million).

Credit risk. We have exposure to credit risk primarily as a holder of fixed income securities and private securities. Our risk management strategy andinvestment policy is to invest mainly in debt instruments of high credit quality issuers. We also invest a portion of the portfolio in securities that are belowinvestment grade or in unrated private securities and other specialty asset classes. We reduce the amount of credit exposure by setting limits with respect toparticular ratings categories, business sectors and any one issuer. As at December 31, 2020, the average rating of fixed income maturities in our investmentportfoliowas“AA-”(December31,2019—“AA-”).

Inaddition,weareexposedtothecreditriskofourinsuranceandreinsurancebrokerstowhomwemakeclaimspaymentsforourpolicyholders,aswellastothe credit risk of our reinsurers and retrocessionaires whoassumebusiness fromus. Other than fully collateralized reinsurance, the substantial majority of ourreinsurers have a rating of “A” (Excellent), the third highest of fifteen rating levels, or better by A.M. Best and the minimum rating of any of our materialreinsurers is “A-” (Excellent), the fourth highest of fifteen rating levels, by A.M. Best. The total amount recoverable by the Company from reinsurers as atDecember31,2020was$3,195.2million(2019—$2,319.8million)ofwhich$2,010millionwasuncollateralized(2019—$1,817.5million).AsatDecember31,2020,oftheCompany’suncollateralizedreinsurancerecoverables,11%(2019—15.1%)werewithMunichRewhichisratedA+byA.M.BestandAA-byS&P,13.4%(2019—11.9%)werewithEverestRewhichisratedA+byA.MBestandA+byS&P,and9.2%(2019—8.9%)werewithLloyd’swhichisratedAbyA.M.BestandA+byS&P.ThesearetheCompany’slargestexposurestoindividualreinsurers.TheCompanyhasmadenoprovisionfordoubtfuldebtsfromanyofitsreinsurersasatDecember31,2020.

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Item 12. Description of Securities Other Than Equity Securities.

Notapplicable.

PART II

Item 13. Defaults, Dividends Arrearages and Delinquencies

None.

Item 14. Material Modifications to the Rights of Security Holders and Use of Proceeds

None.

Item 15. Controls and Procedures

A. Disclosure Controls and Procedures

TheCompany,underthesupervisionandwiththeparticipationoftheCompany’smanagement, includingtheCompany’sChiefExecutiveOfficerandChiefFinancial Officer, has evaluated the design and operation of the Company’s disclosure controls and procedures as of the end of the period of this report. Ourmanagementdoesnotexpectthatourdisclosurecontrolswillpreventallerrorsandallfraud.Acontrolsystem,nomatterhowwellconceivedandoperated,canprovideonlyreasonable,notabsolute,assurancethattheobjectivesofthecontrolsystemaremet.Further,thedesignofacontrolsystemmustreflectthefactthatthereareresourceconstraints,andthebenefitsofcontrolsmustbeconsideredrelativetotheircosts.Asaresultoftheinherentlimitationsinallcontrolsystems,noevaluationofcontrolscanprovideabsoluteassurancethatallcontrolissuesandinstancesoffraud,ifany,withintheCompanyhavebeendetected.Theseinherentlimitationsincludetherealitiesthatjudgmentsindecision-makingcanbefaulty,andthatbreakdownscanoccurbecauseofasimpleerrorormistake.Additionally,controlscanbecircumventedbytheindividualactsofpersonsorbycollusionoftwoormorepeople.Thedesignofanysystemofcontrolsalsoisbasedinpartuponcertainassumptionsaboutthelikelihoodoffutureevents,andtherecanbenoassurancethatanydesignwillsucceedinachievingitsstatedgoalsunderallpotential future conditions. Over time, controls may become inadequate because of changes in conditions, or the degree of compliance with the policies orprocedures maydeteriorate. As a result of the inherent limitations in a cost-effective control system, misstatement due to error or fraud mayoccur and not bedetected.Accordingly,ourdisclosurecontrolsandproceduresaredesignedtoprovidereasonable,notabsolute,assurancethatthedisclosurerequirementsaremet.

Basedontheevaluationofthedisclosurecontrolsandprocedures,theCompany’sChiefExecutiveOfficerandChiefFinancialOfficerhaveconcludedthat,asofDecember31,2020,theCompany’sdisclosurecontrolsandprocedureswereeffectiveinensuringthatinformationrequiredtobedisclosedinthereportsfiledorsubmittedtotheSECundertheExchangeActbytheCompanywererecorded,processed,summarizedandreportedinatimelyfashion,andwereaccumulatedandcommunicated to management, including the Company’s Chief Executive Officer and Chief Financial Officer, to allow timely decisions regarding requireddisclosure.

B. Management’s Annual Report on Internal Control over Financial Reporting

Management is responsible for establishing and maintaining adequate internal control over financial reporting. Internal control over financial reporting isdesignedtoprovidereasonableassuranceregardingthepreparationoffinancialstatementsforexternalpurposesinaccordancewithU.S.GAAP.

Ourmanagementisresponsibleforestablishingandmaintainingadequateinternal controloverfinancial reporting, asisdefinedinExchangeActRule13a-15(f) andas contemplated bySection 404of the Sarbanes-Oxley Act. Our internal control systemwasdesignedto provide reasonable assurance regarding thereliabilityoffinancialreportingandthepreparationoffinancialstatementsforexternalpurposesinaccordancewithgenerallyacceptedaccountingprinciples.Allinternalcontrolsystems,nomatterhowwelldesigned,haveinherentlimitations.Theselimitationsincludethepossibilitythatjudgmentsindecision-makingcanbefaulty and that breakdowns can occur because of error or mistake. Therefore, any internal control systemcan provide only reasonable assurance and may notpreventordetectallmisstatementsoromissions.Inaddition,ourevaluationofeffectivenessisasofaparticularpointintimeandtherecanbenoassurancethatanysystemwillsucceedinachievingitsgoalsunderallfutureconditions.

Management assessed the effectiveness of the Company’s internal control over financial reporting as of December 31, 2020. In making this assessment,managementusedthecriteriasetforthbytheCommitteeofSponsoringOrganizationsoftheTreadwayCommission(“COSO”)inInternal Control - IntegratedFramework (2013). Based on our assessment in accordance with the criteria, we believe that our internal controls over financial reporting were effective as atDecember31,2020.The

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consolidatedfinancialstatementsincludedinthisForm20-Ffairlyrepresentinallmaterialrespectsthefinancialcondition,resultsofoperationsandcashflowsoftheCompanyfortheperiodspresented.

C. Changes in Internal Control Over Financial Reporting

Adverse Development Contract.Duringthecourseof2020,theCompanyenteredintoanADCreinsuranceagreementwithasubsidiaryofEnstar,pursuanttowhichEnstar’ssubsidiarywill reinsurelossesincurredonorpriortoDecember31,2019.Enstar’ssubsidiarywill provide$770.0millionofcoverinexcessof$3.805billionretentionuptoanaggregateof$4.575billion,andanadditional$250.0millionofcoverinexcessabove$4.815billion,upto$5.065billion.AsaresultoftheADC,wehavesignificantlyreducedourexposuretoclaimsfromrisksunderwrittenonorpriortoDecember31,2019,andweexpecttheADCtosignificantlyreducevolatilityfromourhistoricalbusinessgoingforward.During2020,thecompanyestablishedinternalcontrolsoverfinancialreportingtoensuretheaccuracyandcompletenessofADCrelatedbalancesanddisclosures.Additionally,anADCmanagementcommitteehasbeenestablishedwhichmonitorsADCreportedbalancesanddisclosures.

Additional Ceded Premiums. Toremediate the identified material weakness in our internal controls over financial reporting in 2019, wehave increased thescopeofpremiumcontrolsrelatedtoexcessoflosscededreinsurancecontracts,aswellasenhancedcontrolsaroundthedocumentationofadjustmentpremiumsforcededreinsurancecontracts.Wehaveimprovedthesegregationofresponsibilitiesacrossthecededpremiumprocess,whichhasresultedinadditionallayersofmanagementreview.Managementhasconcluded,throughtesting,thatthesenewcontrolsareoperatingeffectively.

Management’sassessmentoftheoveralleffectivenessofourinternalcontrolsoverfinancialreportingwasbasedonthecriteriasetforthinInternal Control —Integrated Framework (2013)issuedbythe Committee of SponsoringOrganizations (“COSO”) of the TreadwayCommission. Baseduponthat evaluation, theCompany’smanagementisnotawareofanyadditionalchanges,otherthantheonesmentionedabove,initsinternalcontroloverfinancialreportingthatoccurredduringtheyearendedDecember31,2020thathasmateriallyaffected,orisreasonablylikelytomateriallyaffect,theCompany’sinternalcontroloverfinancialreporting.

Item 16A. Audit Committee Financial Expert

TheBoard has determined that each of Mr. GordonIreland and Mr. Richard Lightowler is an independent director and audit committee financial expert inaccordancewiththeNYSElistingrules.

Item 16B. Code of Ethics

OurBoardhasadoptedacodeofethicsentitled“CodeofBusinessConductandEthics”whichappliestoallofouremployees,officersanddirectors.CopiesofourCodeofBusinessConductandEthicscanbefoundonourwebsiteatwww.aspen.coandmaybeobtainedinprint,withoutcost,bywritingtoAspenInsuranceHoldingsLimited,Attention:CompanySecretary,141FrontStreet,HamiltonHM19,Bermuda.Weintendtosatisfyapplicabledisclosurerequirementsregardingamendmentsto,orwaiversfrom,provisionsofourCodeofConductbypostingsuchinformationonourwebsitewithinfivebusinessdaysfollowingthedateoftheamendmentorwaiver.

Item 16C. Principal Accountant Fees and Services

Thefollowingtable represents aggregate fees billedtotheCompanybyKPMGLLP(“KPMG”), London, England, theCompany’s independent registeredpublicaccountingfirmandauditor,forfiscalyearsendedDecember31,2020and2019:

Twelve Months EndedDecember 31, 2020

Twelve Months Ended December31, 2019

($inmillions)AuditFees $ 4.13 $ 3.90Audit-RelatedFees 0.40 0.19TaxFees 0.02 0.02AllOtherFees 0.56 0.13TotalFees $ 5.11 $ 4.24

(1) Audit fees consist of fees paid to KPMG for professional services for the audit of the Company’s annual consolidated financial statements, review of quarterlyconsolidatedfinancialstatements,auditofannualstatutorystatements,andforservicesthatarenormallyprovidedbyindependentauditorsinconnectionwithstatutory,comfortletters,SECandregulatoryfilingsorengagements.

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(2)Audit-relatedfeesconsistoffeespaidforassuranceandrelatedservicesfortheperformanceoftheauditorreviewoftheCompany’sfinancialstatements(otherthantheauditfeesdisclosedabove),suchastheauditofSolvencyIIbalancesheetandthe401(k)Plan.

(3)Taxfeesarefeesrelatedtotaxcompliance.

(4) AllotherfeesrelatetofeesbilledtotheCompanybyKPMGfornon-auditservicesrenderedtotheCompanyinconnectionwiththe7.625%/8.375%SeniorSecuredPIKToggleNotesdue2025issuedbyHighlandsHoldingsBondIssuer,Ltd.andHighlandsHoldingsBondCo-Issuer,Inc.

ThepolicyoftheAuditCommitteeistoapproveallauditandpermissiblenon-auditservicestobeprovidedbytheindependentregisteredpublicaccountingfirmduringtheyear.TheAuditCommitteeconsideredwhethertheprovisionofthenon-auditservicesbyKPMGwascompatiblewithmaintainingKPMG’sindependencewithrespecttotheCompanyanddeterminedthattheprovisionofsuchserviceswascompatiblewithKPMGmaintainingitsindependence.TheAuditCommitteeapprovedalloftheservicesprovidedbyKPMGforthefiscalyearendedDecember31,2020.

Item 16D. Exemptions from the Listing Standards for Audit Committee

None.

Item 16E. Purchases of Equity Securities by the Issuer and Affiliated Purchasers

None.

Item 16F. Change in Registrant’s Certifying Accountant

InJune2020,theAuditCommitteeapprovedconductingacompetitiveselectionprocesstodeterminetheCompany’sindependentregisteredpublicaccountingfirmforthefiscalyearendingDecember31,2022.TheCommitteeinvitedseveralinternationalpublicaccountingfirmstoparticipateinthisprocess.Asaresultofthisprocess,theAuditCommitteeintendstoengageErnst&YoungLLP(“EY”)astheCompany’sindependentregisteredpublicaccountingfirmforthefiscalyear endingDecember 31, 2022, subject to completion of its standard client acceptance procedures. KPMGwill remain the Company’s independent registeredpublicaccountingfirmfortheyearendingDecember31,2021.

KPMG’sreports ontheCompany’sconsolidatedfinancial statements asof andfor thefiscal years endedDecember31, 2019and2020didnotcontainanyadverseopinionordisclaimerofopinion,norweretheyqualifiedormodifiedastouncertainty,auditscope,oraccountingprinciples.

DuringthefiscalyearsendedDecember31,2019and2020,andthesubsequentinterimperiodsthroughthedateofthisreport,therewere:(i)nodisagreementsbetweentheCompanyandKPMGonanymatterofaccountingprinciplesorpractices,financialstatementdisclosure,orauditingscopeorprocedurewhich,ifnotresolvedtoKPMG’ssatisfaction,wouldhavecausedKPMGtomakereferencetheretointheirreports;and(ii)no“reportableevents”describedinItem16F(a)(1)(v)ofForm20-F.

TheCompanyhasprovidedKPMGwithacopyoftheforegoingdisclosureandhasrequestedthatKPMGfurnishtheCompanywithaletteraddressedtotheSECstatingwhetheritagreeswithsuchdisclosure.AcopyofKPMG’sletterisattachedasExhibit15.1.

Item 16G. Corporate Governance

Asaforeignprivateissuer, weareentitledtofollowthepracticeofourhomecountry, Bermuda, withrespect tocertaincorporategovernancerequirementsratherthanadheringtothecorporategovernancerequirementsthatareapplicabletoU.S.issuerslistedontheNYSE.Additionally,because100%ofourordinaryshares are owned by Parent and are not listed on the NYSE, we are a “controlled company” within the meaning of NYSE corporate governance standards.ControlledcompaniesarealsoexemptfromcertainNYSEcorporategovernancestandards.

Pursuant to Section 303.A.11 of the NYSE Listed Company Manual, we are required to list the significant differences between our corporate governancepracticesandtheNYSEcorporategovernancestandardsapplicabletoU.S.issuerslistedontheNYSE.Listedbelowarethesignificantdifferences:

• Wedonothaveamajorityofindependentdirectors.TheNYSErequiresU.S.issuerlistedcompaniestohaveaboardofdirectorsofatleastamajorityofindependentdirectors.Controlledcompanies,however,areexemptfromthisrequirement.UnderBermudalawandourBye-Laws,wearenotrequiredtohaveamajorityofindependentdirectors.

• Wedo not have a nominating/corporate governance committee. Instead, the functions typically performed by such a committee are performed by theBoard.TheNYSErequiresU.S.issuerlistedcompaniestohaveanominating/

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corporate governance committee composed entirely of independent directors and a committee charter detailing the committee’s purpose andresponsibilities and an annual performance evaluation of the committee. Controlled companies, however, are exempt from this requirement. UnderBermudalawandourBye-Laws,wearenotrequiredtohaveanominatingorcorporategovernancecommittee.

• Wedonothaveacompensationcommittee. TheNYSErequiresU.S.issuerlistedcompaniestohaveacompensationcommitteecomposedentirelyofindependentdirectorsandacommitteecharterdetailingthecommittee’spurposeandresponsibilities,anannualperformanceevaluationofthecommitteeand the rights and responsibilities of the committee with respect to retaining or obtaining advice froman independent adviser. Controlled companies,however,areexemptfromthisrequirement.UnderBermudalawandourBye-Laws,wearenotrequiredtohaveacompensationcommittee.

Item 16H. Mine Safety Disclosure

Notapplicable.

PART III

Item 17. Financial Statements

RefertoItem18ofthisreport.

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Item 18. Financial Statements

ASPEN INSURANCE HOLDINGS LIMITED

CONSOLIDATED BALANCE SHEETSAs at December 31, 2020 and December 31, 2019

($ in millions, except share and per share amounts)

As at December 31,2020

As at December 31,2019

ASSETSInvestments:

Fixedincomematurities,availableforsale(amortizedcost—$4,126.7and$4,845.2netofallowanceforexpectedcreditlosses$0.2—$Nil) $ 4,348.1 $ 4,958.2Fixedincomematurities,tradingatfairvalue(amortizedcost—$844.8and$1,106.6) 855.6 1,128.8Short-terminvestments,availableforsale(amortizedcost—$88.0and$117.6) 87.8 117.6Short-terminvestments,tradingatfairvalue(amortizedcost—$35.4and$79.2) 35.4 79.2Catastrophebonds,tradingatfairvalue(cost—$18.8and$29.4) 18.8 28.6Privately-heldinvestments,tradingatfairvalue(amortizedcost—$319.7and$279.2) 299.3 279.7Investments,equitymethod 0.9 67.9Otherinvestments 109.4 111.4Totalinvestments 5,755.3 6,771.4

Cashandcashequivalents(includingcashwithinconsolidatedvariableinterestentitiesof—$69.9and$69.1) 1,747.3 1,030.5Reinsurancerecoverables:

Unpaidlosses (netofallowanceforexpectedcreditlossesof$3.8—$Nil) 3,195.2 2,319.8Cededunearnedpremiums 453.7 443.7

Receivables:Underwritingpremiums(netofallowanceforexpectedcreditlossesof$34.0—$Nil) 1,279.8 1,318.4Other 135.2 114.3

Fundswithheld 98.0 85.0Deferredpolicyacquisitioncosts 306.6 291.1Derivativesatfairvalue 26.8 12.9Receivablesforsecuritiessold 1.4 5.1Officepropertiesandequipment 77.4 64.8Right-of-useoperatingleaseassets 74.1 93.5Incometaxrecoverable 3.4 4.5Otherassets 8.4 1.6Intangibleassetsandgoodwill 22.8 23.9

Total assets $ 13,185.4 $ 12,580.5

Includedwithinreinsurancerecoverableforunpaidlossesare$770.0millionofrecoveriesassociatedwiththepurchaseofanadversedevelopmentcover.

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ASPEN INSURANCE HOLDINGS LIMITED

CONSOLIDATED BALANCE SHEETSAs at December 31, 2020 and December 31, 2019

($ in millions, except share and per share amounts)

As at December 31,2020 At December 31, 2019

LIABILITIESInsurancereserves

Lossesandlossadjustmentexpenses $ 7,165.3 $ 6,951.8Unearnedpremiums 1,817.4 1,737.7

Totalinsurancereserves 8,982.7 8,689.5Payables

Reinsurancepremiums 567.5 439.6Incometaxespayable 3.7 2.7Accruedexpensesandotherpayables 214.4 220.8Payablesforsecuritiespurchased — 2.2Operatingleaseliabilities 106.0 113.2Liabilitiesunderderivativecontracts 13.6 87.2Totalpayables 905.2 865.7

Long-termdebt 299.9 299.8Total liabilities $ 10,187.8 $ 9,855.0Commitmentsandcontingentliabilities(seeNote20) — —SHAREHOLDERS’EQUITYOrdinaryshares:

60,395,839sharesofparvalue$0.01each(December31,2019—60,395,839shares) $ 0.6 $ 0.6

Preferenceshares:11,000,0005.950%sharesofparvalue0.15144558¢each(December31,2019—11,000,000) — —10,000,0005.625%sharesofparvalue0.15144558¢each(December31,2019—10,000,000) — —10,0005.625%sharesofparvalue0.15144558¢each,representedby10,000,000depositaryshares,eachrepresenting1/1000thinterestinonepreferenceshare(December31,2019—10,000) — —

Non-controllinginterest — —Additionalpaid-incapital 1,469.7 1,201.7Retainedearnings 1,425.7 1,514.6Accumulatedothercomprehensiveincome,netoftaxes 101.6 8.6

Total shareholders’ equity 2,997.6 2,725.5Total liabilities and shareholders’ equity $ 13,185.4 $ 12,580.5

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ASPEN INSURANCE HOLDINGS LIMITED

CONSOLIDATED STATEMENTS OF OPERATIONS AND OTHER COMPREHENSIVE INCOMEFor The Twelve Months Ended December 31, 2020, 2019 and 2018

($ in millions, except share and per share amounts) Twelve Months Ended December 31, 2020 2019 2018RevenuesNetearnedpremium $ 2,532.6 $ 2,293.3 $ 2,214.7Netinvestmentincome 154.6 197.3 198.2Realizedandunrealizedinvestmentgains 98.5 97.1 110.0Otherincome 49.8 4.9 9.0

Totalrevenues 2,835.5 2,592.6 2,531.9ExpensesLossesandlossadjustmentexpenses 1,840.8 1,679.7 1,573.0Amortizationofdeferredpolicyacquisitioncosts 465.7 412.7 371.6General,administrativeandcorporateexpenses 410.9 521.6 491.7Interestonlong-termdebt 33.9 20.2 25.9Changeinfairvalueofderivatives 65.1 144.2 31.8Changeinfairvalueofloannotesissuedbyvariableinterestentities — 3.1 4.4Realizedandunrealizedinvestmentlosses 27.4 10.9 174.7Realizedlossondebtextinguishment — 5.5 8.6Netrealizedandunrealizedforeignexchangelosses 12.4 11.8 3.5Otherexpenses 10.8 1.7 2.7

Totalexpenses 2,867.0 2,811.4 2,687.9(Loss)fromoperationsbeforeincometaxes (31.5) (218.8) (156.0)Incometax(expense)/benefit (8.6) (22.9) 10.2

Net(loss) $ (40.1) $ (241.7) $ (145.8)Amountattributabletonon-controllinginterest — 1.2 (1.0)Net (loss) attributable to Aspen Insurance Holdings Limited’s ordinary shareholders $ (40.1) $ (240.5) $ (146.8)Other Comprehensive Income/(Loss):Availableforsaleinvestments:Reclassificationadjustmentfornetrealized(losses)/gainsoninvestmentsincludedinnetincome $ (67.1) $ (6.8) $ 5.2Changeinnetunrealizedgains/(losses)onavailableforsalesecuritiesheld 175.6 171.7 (86.5)Netchangefromcurrentperiodhedgedtransactions 0.3 4.8 (2.1)Changeinforeigncurrencytranslationadjustment (9.6) (28.0) 21.5

Othercomprehensiveincome/(loss),grossoftax 99.2 141.7 (61.9)Incometax(expense)/benefitthereon:Reclassificationadjustmentfornetrealizedlossesoninvestmentsincludedinnetincome — — (0.7)Changeinnetunrealizedgainsonavailableforsalesecuritiesheld (6.2) (13.6) 5.5Netchangefromcurrentperiodhedgedtransactions — (0.8) 0.3Changeinforeigncurrencytranslationadjustment — 3.2 (9.2)

Totalincometaxexpenseallocatedtoothercomprehensive(loss) (6.2) (11.2) (4.1)Othercomprehensiveincome/(loss),netoftax 93.0 130.5 (66.0)

Total comprehensive income/(loss) attributable to Aspen Insurance Holdings Limited’s ordinaryshareholders $ 52.9 $ (110.0) $ (212.8)

2020includesthegainonsaleofourrenewalrightsonoursuretyinsurancebookofbusinesstoathirdparty,totaling$43.1million.

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ASPEN INSURANCE HOLDINGS LIMITED

CONSOLIDATED STATEMENTS OF CHANGES IN SHAREHOLDERS’ EQUITYFor The Twelve Months Ended December 31, 2020, 2019 and 2018

($ in millions) Twelve Months Ended December 31, 2020 2019 2018 (3)

OrdinarysharesBeginningoftheyear $ 0.6 $ 0.1 $ 0.1Ordinarysharescanceled — (0.1) —Newordinarysharesissued — 0.6 —Endoftheyear 0.6 0.6 0.1

PreferencesharesBeginningandendoftheyear — — —

Non-controllinginterestBeginningoftheyear — 3.7 2.7Netchangeattributabletonon-controllinginterestfortheyear — (1.2) 1.0Minorityinterestbuy-out — (2.5) —Endoftheyear — — 3.7

Additionalpaid-incapitalBeginningoftheyear 1,201.7 967.5 954.7Newordinarysharesissued — 0.8 2.7Capitalcontribution 268.0 — —Preferencesharesissued — 241.6 —Share-basedcompensation — (9.9) 10.1Minorityinterestconsideration — (0.8) —Minorityinterestbuy-out — 2.5 —Endoftheyear 1,469.7 1,201.7 967.5

RetainedearningsBeginningoftheyear 1,514.6 1,791.0 2,011.3Net(loss)fortheyear (40.1) (241.7) (145.8)Dividendsonordinaryshares — — (42.9)Dividendsonpreferenceshares (44.5) (35.9) (30.5)Netchangeattributabletonon-controllinginterestfortheyear — 1.2 (1.0)Dividendsduetonon-controllinginterest — — (0.1)Openingcreditlosses(“CECL”) (4.3) — —Endoftheyear 1,425.7 1,514.6 1,791.0

Accumulatedothercomprehensiveincome:Cumulativeforeigncurrencytranslationadjustments,netoftaxes:

Beginningoftheyear (80.2) (55.4) (67.7)Changefortheyear,netofincometax (9.6) (24.8) 12.3Endoftheyear (89.8) (80.2) (55.4)

Gainonderivatives,netoftaxes:Beginningoftheyear 4.3 0.3 2.1Netchangefromcurrentperiodhedgedtransactions 0.3 4.0 (1.8)Endoftheyear 4.6 4.3 0.3

Unrealizedappreciationonavailableforsaleinvestments,netoftaxes:Beginningoftheyear 84.5 (66.8) 9.7Changefortheyear,netoftaxes 102.3 151.3 (76.5)Endoftheyear 186.8 84.5 (66.8)

Totalaccumulatedothercomprehensiveincome/(loss),netoftaxes 101.6 8.6 (121.9)

Total shareholders’ equity $ 2,997.6 $ 2,725.5 $ 2,640.4

The$268.0millionrelatestoadditionalcapitalcontributionreceivedfromourparentcompanyHighlandsBermudaHoldco,Ltd.Thebalancein2018of$10.1millionisareclassificationfromaccruedexpensesandotherpayablesasaresultofthenetsettlementofrestrictedshareunitsfollowingtheadoptionofASU2016-09-“Compensation — Stock

Compensation”.Thebalancein2019of$(9.9)millionrelatestothereclassificationfromadditionalpaid-incapitaltoaccruedexpensesandotherpayablesasaresultofthenetsettlementoftaxesonrestrictedshareunits.AsoftheyearendDecember31,2019,theretainedearningswasrestatedby$15.6millionfromJanuary1,2017toaccountforadditionalcededpremiumsonexcessoflosscededreinsurancecontractsforperiodsDecember31,

2016andprior.The$4.3millionrelatestothecumulativeeffect-adjustmenttoopeningretainedearningsasaresultoftherecognitionofcurrentexpectedcreditlosses(‘CECL’)intheCompany’savailable-for-saleinvestmentportfolioand

reinsurancerecoverablesfollowingtheadoptionofASU2016-13.

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ASPEN INSURANCE HOLDINGS LIMITED

CONSOLIDATED STATEMENTS OF CASH FLOWSFor The Twelve Months Ended December 31, 2020, 2019 and 2018

($ in millions) Twelve Months Ended December 31, 2020 2019 2018Cash flows (used in)/from operating activities:Net(loss) $ (40.1) $ (241.7) $ (145.8)Proportionduetonon-controllinginterest — 1.2 (1.0)Adjustmentstoreconcilenetincometonetcashflowsfromoperatingactivities:Depreciationandamortization 45.8 39.8 43.4Impairmentofleaseassets 12.9 12.3 —Amortizationofright-to-useoperatingleaseassets 11.8 13.4 —Interestonoperatingleaseliabilities 5.5 4.6 —Share-basedcompensation — — 10.1Realizedandunrealizedinvestment(gains) (98.5) (97.1) (110.0)Realizedandunrealizedinvestmentlosses 27.4 10.9 174.7Deferredtaxexpense/(benefit) (5.7) 24.7 (7.1)Changeinfairvalueofloannotesissuedbyvariableinterestentities — 3.1 4.4Netrealizedandunrealizedinvestmentforeignexchange(gains)/losses (23.1) 28.1 (0.8)Netchangefromcurrentperiodhedgedtransactions 0.3 4.8 (1.8)Changesin:

Insurancereserves:Lossesandlossadjustmentexpenses 146.9 (203.0) 402.5Unearnedpremiums 68.0 18.0 (91.6)

Reinsurancerecoverables:Unpaidlosses (864.9) (236.3) (575.8)Cededunearnedpremiums (9.6) 116.0 (44.8)

Otherreceivables (17.4) (0.4) 29.9Deferredpolicyacquisitioncosts (13.3) (41.1) 41.7Reinsurancepremiumspayable 129.7 19.5 52.1Fundswithheld (13.0) 6.8 8.0Premiumsreceivable 71.2 144.8 31.6Incometaxpayable 2.5 (1.2) 1.6Accruedexpensesandotherpayable 2.4 (19.3) (88.2)Fairvalueofderivativesandsettlementofliabilitiesunderderivatives (87.5) 73.8 5.9Long-termdebtandloannotesissuedbyvariableinterestentities 0.1 0.1 (44.0)Operatingleaseliabilities (17.3) (18.0) —Otherassets (6.8) (1.6) 0.5Net cash (used in) operating activities $ (672.7) $ (337.8) $ (304.5)

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ASPEN INSURANCE HOLDINGS LIMITED

CONSOLIDATED STATEMENTS OF CASH FLOWSFor The Twelve Months Ended December 31, 2020, 2019 and 2018

($ in millions) Twelve Months Ended December 31, 2020 2019 2018Cash flows from investing activities: (Purchases)offixedincomesecurities—Availableforsale $ (1,632.0) $ (1,650.7) $ (1,785.6)(Purchases)offixedincomesecurities—Trading (281.9) (1,169.1) (1,260.9)Proceedsfromsalesandmaturitiesoffixedincomesecurities—Availableforsale 2,415.8 2,105.3 1,647.1Proceedsfromsalesandmaturitiesoffixedincomesecurities—Trading 554.4 1,302.7 1,661.0(Purchases)ofequitysecurities—Trading — — (16.5)Netproceeds/(purchases)ofcatastrophebonds—Trading 9.8 7.5 (4.1)Proceedsfromsalesofequitysecurities—Trading — — 505.6(Purchases)ofshort-terminvestments—Availableforsale (216.1) (182.7) (130.8)Proceedsfromsaleofshort-terminvestments—Availableforsale 246.1 159.0 113.2(Purchases)ofshort-terminvestments—Trading (58.3) (193.6) (16.4)Proceedsfromsaleofshort-terminvestments—Trading 103.8 141.1 78.9(Purchases)ofprivately-heldinvestments—Trading (92.8) (287.3) —Proceedsfromsaleofprivately-heldinvestments—Trading 64.9 9.8 —Netchangein(payable)/receivableforsecurities(purchased)/sold 1.5 (0.4) (5.5)(Purchases)ofotherinvestments—realestatefund — — (100.0)Netproceedsfromsalesofotherinvestments 71.1 — —(Net)purchasesofequipment (40.7) (22.2) (27.3)InvestmentinMultilinereinsurer (0.5) — —Netsales/(purchases)ofinvestments,equitymethod 6.1 (1.1) (1.4)

Net cash from investing activities 1,151.2 218.3 657.3Cash flows from/(used in) financing activities:Proceedsfromtheissuanceofordinaryshares,netofissuancecosts — 1.4 2.7Ordinarysharescanceled — (0.1) —Capitalcontribution 268.0 — —Preferenceshareissuance — 241.6 —Minorityinterestbuy-out — (0.8) —Repaymentoflong-termdebtissuedbySilverton — (7.7) (86.4)Dividendspaidonordinaryshares — — (42.9)Dividendspaidonpreferenceshares (44.5) (35.9) (30.5)Dividendspaidtonon-controllinginterest — — (0.1)Contingentconsideration-earnoutprovisionsettlement — — (11.7)Long-termdebtredeemed — (125.0) (125.0)Make-wholepayment — (5.5) (8.6)Cashpaidfortaxwithholdingpurposes — (2.8) (4.7)

Net cash from/(used in) financing activities 223.5 65.2 (307.2)

Effectofexchangeratemovementsoncashandcashequivalents 14.8 1.1 (16.7)

Increase/(decrease)incashandcashequivalents 716.8 (53.2) 28.9Cashandcashequivalentsatbeginningofperiod 1,030.5 1,083.7 1,054.8Cash and cash equivalents at end of period $ 1,747.3 $ 1,030.5 $ 1,083.7

Supplementaldisclosureofcashflowinformation:Netcashpaid/(received)duringtheperiodforincometaxes $ 15.0 $ (4.7) $ (0.3)Cashpaidduringtheperiodforinterest $ 14.0 $ 19.0 $ 25.3

____________________

Thecashpaidtothetaxauthoritywhenwithholdingsharesfromemployees’awardsfortax-withholdingpurposeshasbeenreclassifiedfromoperatingactivitytofinancingactivityfollowingtheadoptionofASU2016-09-“Compensation — Stock Compensation”.

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ASPEN INSURANCE HOLDINGS LIMITED

NOTES TO THE AUDITED CONSOLIDATED FINANCIAL STATEMENTSFor The Twelve Months Ended December 31, 2020, 2019 and 2018

($ in millions, except share and per share amounts)

1. History and OrganizationHistory and Organization. AspenInsuranceHoldingsLimited(“AspenHoldings”)wasincorporatedonMay23,2002asaholdingcompanyheadquartered

inBermuda.WeunderwritespecialtyinsuranceandreinsuranceonaglobalbasisthroughourOperatingSubsidiaries(asdefinedbelow)basedinBermuda,theUnitedStates andthe UnitedKingdom:AspenInsuranceUKLimited(“AspenU.K.”) andAspenUnderwritingLimited(“AUL”)(as corporate member of ourLloyd’s operations, which are managed by Aspen Managing Agency Limited (“AMAL”)), Aspen Bermuda Limited (“Aspen Bermuda”), Aspen SpecialtyInsuranceCompany(“AspenSpecialty”)andAspenAmericanInsuranceCompany(“AAIC”)(eachreferredtohereinan“OperatingSubsidiary”andcollectivelyreferredtoasthe“OperatingSubsidiaries”).WealsohavebranchesinAustralia,Canada,SingaporeandSwitzerland.WeestablishedAspenCapitalManagement,Ltd.andotherrelatedentities(collectively,“ACM”)toleverageourexistingunderwritingfranchise,increaseouroperationalflexibilityinthecapitalmarketsandprovideinvestorsdirectaccesstoourunderwritingexpertise.Referencestothe“Company,”the“Group,”“we,”“us”or“our”refertoAspenHoldingsorAspenHoldingsanditsconsolidatedsubsidiaries.

On February 15, 2019, the Company completed its merger with Highlands Merger Sub, Ltd. (“Merger Sub”), a wholly owned subsidiary of HighlandsBermuda Holdco, Ltd. (formerly known as Highlands Holdings, Ltd.) (“Parent”). Merger Sub merged with and into the Company (the “Merger”), with theCompany continuing as the surviving company and as a wholly owned subsidiary of Parent. Parent, a Bermuda exempted company, is an affiliate of certaininvestment fundsmanagedbyaffiliates ofApolloGlobal Management, Inc., a leadingglobal investment manager (collectively withits subsidiaries, “Apollo”).Additional information about the Merger is set forth in the Company’s Current Report on Form 8-K filed with the United States Securities and ExchangeCommission(the“SEC”)onFebruary15,2019andtheexhibitsthereto,andonAugust28,2018andtheexhibitsthereto,includingtheMergerAgreement,andtheCompany’sdefinitiveproxystatementonSchedule14AfiledwiththeSEConNovember6,2018.

As a result of the Merger, all of the Company’s publicly traded ordinary shares were automatically canceled. The ordinary shares of the Company ceasedtradingontheNewYorkStockExchange(“NYSE”)priortotheopeningoftradingonFebruary15,2019.TheCompany’spreferencesharesanddepositarysharescontinuetobelistedontheNYSEunderthefollowingsymbols:AHLPRC,AHLPRDandAHLPRE.

2. Basis of Presentation and Significant Accounting PoliciesThe consolidated financial statements of Aspen Holdings are prepared in accordance with United States Generally Accepted Accounting Principles

(“U.S.GAAP”)andarepresentedonaconsolidatedbasisincludingthetransactionsofalloperatingsubsidiariesinwhichtheCompanyhasacontrollingfinancialinterest andvariable interest entities (“VIE”) inwhichtheCompanyis consideredtobetheprimarybeneficiary. TransactionsbetweenAspenHoldingsanditssubsidiariesareeliminatedwithintheconsolidatedfinancialstatements.

The consolidated financial statements have been compiled on a going concern basis. The consolidated financial statements are presented in U.S. dollarmillionsandallvaluesareroundedto1decimalpointexceptwhereotherwiseindicated.

(a)Use of EstimatesAssumptionsandestimatesmadebymanagementhasasignificant effect ontheamountsreportedwithintheconsolidatedfinancial statements. Themost

significantoftheserelatetolossesandlossadjustmentexpenses,reinsurancerecoverables,grosswrittenpremiumsandcommissionswhichhavenotbeenreportedtotheCompanysuchasthoserelatingtoproportionaltreatyreinsurancecontracts,unrecognizedtaxbenefits,recoverabilityofdeferredtaxbalances,thefairvalueofderivativesandthefairvalueofotherandprivately-heldinvestments.Allmaterialassumptionsandestimatesareregularlyreviewedandadjustmentsmadeasnecessarybutactualresultscouldbesignificantlydifferentfromthoseexpectedwhentheassumptionsorestimatesweremade.

(b)Accounting for Insurance and Reinsurance OperationsPremiums Earned.Premiumsarerecordedaswrittenontheinceptiondateofapolicy.Premiumsareprimarilyrecognizedasrevenuesproportionatelyover

thecoverageperiod.Premiumsearnedarerecordedinthestatementsofoperations,netofthecostofpurchasedreinsurance.Premiumswrittenwhicharenotyetrecognizedasearnedpremiumarerecordedintheconsolidatedbalancesheetasunearnedpremiums,grossofanycededunearnedpremiums.Writtenandearnedpremiumsandtherelatedcostsincludeestimatesforpremiumswhichhavenotbeenfinallydetermined.Theserelatemainlytocontractual

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provisions for the payment of adjustment or additional premiums, premiums payable under proportional treaties and delegated underwriting authorities, andreinstatementpremiums.

Adjustment and additional premiums are premiums charged which relate to experience during the policy term. The proportion of adjustable premiumsincludedinthepremiumestimatesvariesbetweenbusinesslineswiththelargestadjustmentpremiumsbeinginpropertyandcasualtyreinsurance,marine,aviationandenergyinsuranceandthesmallestinpropertyandcasualtyinsurance.

PremiumsunderproportionaltreatycontractsanddelegatedunderwritingauthoritiesaregenerallynotreportedtotheCompanyuntilafterthereinsurancecoverageisinforce.Asaresult,anestimateofthese“pipeline”premiumsisrecorded.TheCompanyestimatespipelinepremiumsbasedonprojectionsofultimatepremiumtakingintoaccountreportedpremiumsandexpecteddevelopmentpatterns.

Reinstatementpremiumsonassumedexcessoflossreinsurancecontractsareprovidedbasedonexperienceundersuchcontracts.Reinstatementpremiumsarethepremiumschargedfortherestorationofthereinsurancelimitofanexcessoflosscontracttoitsfullamountafterpaymentbythereinsureroflossesasaresult of an occurrence. Reinstatement premiums are recognized as revenue in full at the date of loss, triggering the payment of the reinstatement premiums.Reinstatementpremiumsprovidefutureinsurancecoverfortheremainderoftheinitial policyterm.Anallowanceforuncollectiblepremiumsisestablishedforpossiblenon-paymentofpremiumreceivables,asdeemednecessary.

Outward reinsurance premiums, which are paid when the Company purchases reinsurance or retrocessional coverage, are accounted for using the sameaccountingmethodologyastheCompanyusesforinwardspremiums.Premiumspayableunderreinsurancecontractsthatoperateona“lossesoccurringduring”basisareaccountedforinfullovertheperiodofcoveragewhilethosearisingfrom“risksattachingduring”policiesareexpensedovertheearningsperiodoftheunderlyingpremiumsreceivable fromthereinsuredbusiness. Adjustment premiumsandreinstatement premiumsinrelationtooutwardreinsuranceareaccruedwhen it is determined that the ultimate losses will trigger a payment and recognized within premiums payable. Premiums payable for retroactive reinsurancecoverageandmeetingtheconditionsofreinsuranceaccountingarereportedasreinsurancerecoverablestotheextentthatthoseamountsdonotexceedrecordedliabilitiesrelatingtounderlyingreinsurancecontracts.Totheextentthatrecordedliabilitiesonanunderlyingreinsurancecontractexceedpremiumspayableforretroactivecoverage,adeferredgainisrecognized.

Credit Losses on Underwriting Premiums Receivable. Underwritingpremiumreceivablebalancesarereportednetofanallowanceforexpectedcreditlosses.Theallowance,basedonongoingreviewandmonitoringofamountsoutstanding,historicallossdata,includingwrite-offsandotherrelevantfactors,ischargedtonetincomeintheperiodthereceivableisrecordedandrevisedinsubsequentperiodstoreflectchangesintheCompany’sestimateofexpectedcreditlosses.CreditriskispartiallymitigatedbytheCompany’sabilitytocancelthepolicyifthepolicyholderdoesnotpaythepremium.

Losses and Loss Adjustment Expenses.Lossesrepresenttheamountpaidorexpectedtobepaidtoclaimantsinrespectofeventsthathaveoccurredonorbeforethebalancesheetdate.Thecostsofinvestigating,resolvingandprocessingtheseclaimsareknownaslossadjustmentexpenses(“LAE”).Thestatementofoperations records these losses net of reinsurance, meaning that gross losses and loss adjustment expenses incurred are reduced by the amounts recovered orexpectedtoberecoveredunderreinsurancecontracts.

Reinsurance.Writtenpremiums,earnedpremiums,incurredclaims,LAEandtheamortizationofdeferredpolicyacquisitioncostsallreflecttheneteffectofassumedandcededreinsurancetransactions.AssumedreinsurancereferstotheCompany’sacceptanceofcertaininsurancerisksthatotherinsurancecompanieshaveunderwritten.CededreinsurancearisesfromcontractsunderwhichotherinsurancecompaniesagreetosharecertainriskswiththeCompany.

Reinsurance accounting is followed when there is significant timing risk, significant underwriting risk and a reasonable possibility of significant loss.Reinsuranceandretrocessiondoesnotisolatethecedingcompanyfromitsobligationstopolicyholders. Intheevent that areinsurer orretrocessionaire fails tomeetitsobligations,thecedingcompany’sobligationsremain.TheCompanyregularlyevaluatesthefinancialconditionofitsreinsurersandretrocessionairesandmonitorstheconcentrationofcreditrisktominimizeitsexposuretofinanciallossfromreinsurers’andretrocessionaires’insolvencybyestablishinganallowanceforexpectedcreditlossestoberecognizedoverthelifeofthereinsurancerecoverable.

Reserves.InsurancereservesareestablishedforthetotalunpaidcostofclaimsandLAEinrespectofeventsthathaveoccurredbythebalancesheetdate,includingtheCompany’sestimatesofthetotalcostofclaimsincurredbutnotyetreported(“IBNR”).Claimreservesarereducedforestimatedamountsofsalvageandsubrogationrecoveries.EstimatedamountsrecoverablefromreinsurersonunpaidlossesandLAEarereflectedasassets.

For reported claims, reserves are established on a case-by-case basis within the parameters of coverage provided in the insurance policy or reinsuranceagreement.ForIBNRclaims,reservesareestimatedusinganumberofestablishedactuarialmethodstoestablisharangeofestimatesfromwhichamanagementbest estimate is selected. Both case and IBNRreserve estimates consider variables such as past loss experience, changes in legislative conditions, changes injudicialinterpretationoflegalliability,policycoveragesandinflation.

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Asmanyofthecoveragesunderwritteninvolveclaimsthatmaynotbeultimatelysettledformanyyearsaftertheyareincurred,subjectivejudgmentsastotheultimateexposuretolossesareanintegralandnecessarycomponentofthelossreservingprocess.TheCompanyregularlyreviewsitsreserves,usingavarietyof statistical and actuarial techniques to analyze current claims costs, frequency and severity data, and prevailing economic, social and legal factors. Reservesestablishedinpriorperiodsareadjustedasclaimexperiencedevelopsandnewinformationbecomesavailable.Adjustmentstopreviouslyestimatedreservesarereflectedinthefinancialresultsoftheperiodinwhichtheadjustmentsaremade.

Theprocessofestimatingrequiredreservesdoes,byitsverynature,involveconsiderableuncertainty.Thelevelofuncertaintycanbeinfluencedbyfactorssuchastheexistenceofcoveragewithlongdurationpaymentpatternsandchangesinclaimshandlingpractices,aswellasthefactorsnotedabove.UltimateactualpaymentsforclaimsandLAEcouldturnouttobesignificantlydifferentfromtheCompany’sestimates.

Credit Losses on Reinsurance Recoverables. Amounts recoverable fromreinsurers are estimated in a manner consistent with the claimliability with thereinsuredbusiness.TheCompanyevaluatesthefinancialconditionofitsreinsurersandmonitorsconcentrationofcreditrisktominimizeitsexposuretosignificantlossesfromindividualreinsurers.Tofurtherreducecreditexposureonreinsurancerecoverables,theCompanyhasreceivedcollateral, includinglettersofcreditandtrustaccounts,fromcertainreinsurers.FollowingtheadoptionofASC326,asdescribedabove,anallowanceisestablishedforexpectedcreditlossestoberecognizedoverthelifeofthereinsurancerecoverable.Theallowanceisbaseduponthecurrentfinancialstrengthoftheindividualreinsurerandtheamountofcollateralheld.

Amortization of Deferred Policy Acquisition Costs.Thecostsdirectlyrelatedtowritinganinsurancepolicyarereferredtoaspolicyacquisitionexpensesandincludecommissions,premiumtaxesandprofitcommissions.Withtheexceptionofprofitcommissions,theseexpensesareincurredwhenapolicyisissued,andonlythecostsdirectlyrelatedtothesuccessfulacquisitionofnewandrenewalinsuranceandreinsurancecontractsaredeferredandamortizedoverthesameperiodasthecorrespondingpremiumsarerecordedasrevenues.Profitcommissionsareestimatedbasedontherelatedperformancecriteriaevaluatedatthebalancesheetdate,withsubsequentchangestothoseestimatesrecognizedwhentheyoccur.

Onaregularbasisarecoverabilityanalysisisperformedofthedeferredpolicyacquisitioncostsinrelationtotheexpectedrecognitionofrevenues,includinganticipated investment income, and adjustments, if any, are reflected as period costs. Should the analysis indicate that the acquisition costs are unrecoverable,furtheranalysesareperformedtodetermineifareserveisrequiredtoprovideforlosseswhichmayexceedtherelatedunearnedpremium.

General, Administrative and Corporate Expenses.Thesecosts represent theexpensesincurredinrunningthebusinessandinclude, butarenotlimitedtocompensation costs for employees, rental costs, IT development and operating costs and professional and consultancy fees. General, policy and administrativecostsdirectlyattributabletothesuccessfulacquisitionofbusinessaredeferredandamortizedoverthesameperiodasthecorrespondingpremiumsarerecordedasrevenues.Whenreportingtheresultsforitsbusinesssegments,theCompanyincludesexpenseswhicharedirectlyattributabletothesegmentplusanallocationofcentraladministrativecosts.CorporateexpensesarenotallocatedtotheCompany’sbusinesssegmentsastheytypicallydonotfluctuatewiththelevelsofpremiumwrittenandarerelatedtotheCompany’soperationswhichincludegroupexecutivecosts,groupfinancecosts,grouplegalandactuarialcostsandcertainstrategicandothercosts.

(c)Accounting for Investments, Cash and Cash EquivalentsFixed Income Securities. The fixed income securities portfolio comprises securities issued by governments and government agencies, corporate bonds,

mortgageandotherasset-backedsecuritiesandbankloans.Investmentsinfixedincomesecuritiesareclassifiedasavailableforsaleortradingandarereportedatestimated fair value in the consolidated balance sheet. Investment transactions are recorded onthe trade date with balances pendingsettlement reflected in theconsolidated balance sheet under receivables for securities sold andaccruedexpenses andother payables for securities purchased, respectively. Fair values arebasedonquotedmarketpricesandotherdataprovidedbythird-partypricingservices.

Short-term Investments.Short-terminvestmentsprimarilycomprisehighlyliquiddebtsecuritieswithamaturitygreaterthanthreemonthsbutlessthanoneyearfromthedateofpurchaseandareheldaspartoftheinvestmentportfoliooftheCompany.Short-terminvestmentsareclassifiedaseithertradingoravailableforsaleandcarriedatestimatedfairvalue.

Catastrophe Bonds. Investmentsincatastrophebondsareclassifiedastradingandarecarriedontheconsolidatedbalancesheetatestimatedfairvalue.Thefairvaluesarebasedonindependentbroker-dealerquotes.

Privately-held Investments. The Company’s privately-held investments primarily comprise commercial mortgage loans and middle market loans. Theseinvestmentsareclassifiedastradingandarecarriedontheconsolidatedbalancesheetatestimatedfairvalue.Privately-heldinvestmentsareinitiallyvaluedatcostortransactionvaluewhichapproximatesfairvalue.Insubsequentmeasurementperiods,thefairvaluesofthesesecuritiesareprimarilydeterminedusinginternallydevelopeddiscountedcashflowmodels.Interestincomeisaccruedontheprincipalamountoftheloanbasedonitscontractualinterestratesubjecttoit beingprobable that we will receive interest on that particular underlying loan. Interest income, amortization of premiums and discounts, and prepayment fees arereportedinnetinvestmentincomeontheconsolidatedstatementsofincome.

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Other Investments, Equity Method.Other investments represent the Company’s investments that are recorded using the equity method of accounting.Adjustmentstothefairvalueoftheseinvestmentsaremadebasedonthenetassetvalueoftheinvestment.

Other investments. OtherinvestmentsrepresenttheCompany’sinvestmentinarealestatefund.Adjustmentstothefairvaluearemadebasedonthenetassetvalueoftheinvestment.

Cash and Cash Equivalents.Cashandcashequivalentsarecarriedatfairvalue.Cashandcashequivalentscomprisecashonhand,depositsheldoncallwithbanksandothershort-termhighlyliquidinvestmentsduetomaturewithinthreemonthsfromthedateofpurchaseandwhicharesubjecttoinsignificantriskofchangeinfairvalue.

Gains and Losses.Realizedgainsorlossesonthesaleofinvestmentsaredeterminedonthebasisofthefirstinfirstoutcostmethodand,forfixedincomeavailableforsalesecurities,includeadjustmentstothecostbasisofinvestmentsfordeclinesinvaluethatareconsideredtobeother-than-temporary.Unrealizedgains and losses represent the difference between the cost, or the cost as adjusted by amortization of any difference between its cost and its redemption value(“amortizedcost”),ofthesecurityanditsfairvalueatthereportingdateandareincludedwithinothercomprehensiveincomeforsecuritiesclassifiedasavailableforsaleandinrealizedandunrealizedinvestmentgainsorlossesintheconsolidatedstatementofoperationsforsecuritiesclassifiedastrading.

Current Expected Credit Losses (“CECL”) / Other-than-temporary Impairment of Investments. Following the Company’s adoption of ASU 2016-13“Financial Instruments - Credit Losses (Topic 326)”,effectiveJanuary1,2020,creditlossesonavailableforsaledebtsecuritiesaccountingpolicyisapplicable;priortothisdate,thecomparativeperiodspresentedtheother-than-temporaryimpairmentofinvestmentaccountingpolicywhichwasapplicable:

Credit Losses on Available for Sale Debt Securities. A detailed analysis is performed each reporting period end to assess declines in the fair values ofavailableforsaledebtsecurities.Ourcreditlossmodelemploysadiscountedcashflowapproachacrossallassetclasses.Creditlossesareonlycomputedforassetsheldatanunrealizedlossatthebalancesheetdateandwillhaveafairvaluefloor.DefaultprobabilitiesareestimatedforeachratingfromAAAtoCandanalysisisundertakenseparatelyfordifferentassetsclassesandgeographies.Theexpectedcreditlosses,andsubsequentadjustmentstosuchlossesarerecordedwithinnetrealized gains/(losses) andare deductedfromthe amortized cost basis of the financial asset, with the net carryingvalue of the financial asset presentedontheconsolidatedbalancesheetattheamountexpectedtobecollected.

Other-than-temporary Impairment of Investments. Asecurityisimpairedwhenitsfairvalueisbelowitscostoramortizedcost.TheCompanyrevieweditsinvestment portfolio each quarter on an individual security basis for potential other-than-temporary impairment (“OTTI”) based on criteria including issuer-specificcircumstances,creditratingsactionsandgeneralmacro-economicconditions.

OTTIwasdeemedtooccurwhentherewasnoobjectiveevidencetosupportrecoveryinvalueofasecurityand(i)theCompanyintendedtosellthesecurityormorelikelythannotwouldberequiredtosellthesecuritybeforerecoveryofitscostoradjustedamortizedcostbasisor(ii)itwasdeemedprobablethattheCompany would be unable to collect all amounts due according to the contractual terms of the individual security. In the first case, the entire unrealized losspositionwastakenasanOTTIchargetorealizedlossesinearnings.Inthesecondcase,theunrealizedlosswasseparatedintotheamountrelatedtocreditlossandtheamountrelatedtoall other factors. TheOTTIchargerelatedtocredit loss wasrecognizedinrealizedlossesinearningsandtheamountrelatedtoall otherfactorswasrecognizedinothercomprehensiveincome.Thecostbasisoftheinvestmentisreducedaccordinglyandnoadjustmentstothecostbasisweremadeforsubsequentrecoveriesinvalue.

AlthoughtheCompanyreviewedeachsecurityonacasebycasebasis,ithadalsoestablishedparametersfocusingontheextentanddurationofimpairmenttohelpidentifysecuritiesinanunrealizedlosspositionwhichwereother-than-temporarilyimpaired.Forfixedincomesecuritiesintheavailableforsaleportfolio,theCompanyconsideredsecuritieswhichhadbeeninanunrealizedlosspositionfor12monthsormorewhichhadamarketvalueofmorethan20%belowcostshouldbeother-than-temporarilyimpaired.

Investment Income.Investment incomeincludesamountsreceivedandaccruedinrespect of periodicinterest (“coupons”) payabletotheCompanybytheissueroffixedincomesecurities,equitydividendsandinterestcreditedoncashandcashequivalents.Italsoincludesamortizationofpremiumandaccretionofdiscountinrespectoffixedincomesecurities.Investmentmanagementandcustodyfeesarechargedagainstnetinvestmentincomereportedintheconsolidatedstatementofoperations.

(d)Accounting for Derivative Financial InstrumentsTheCompanyenters intoderivativeinstruments suchasinterest rate swapsandforwardexchangecontracts inorder tomanagecertainmarket andcredit

risks. The Company records derivative instruments at fair value on the Company’s balance sheet as either assets or liabilities, depending on their rights andobligations.

Theaccountingforthegainorlossduetothechangesinthefairvalueoftheseinstrumentsisdependentonwhetherthederivativequalifiesasahedge.Ifthederivative does not qualify as a hedge, the gains or losses are reported in earnings when they occur. If the derivative does qualify as a hedge, the accountingtreatmentvariesbasedonthetypeofriskbeinghedged.

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(e) Accounting for Intangible AssetsIntangibleassetsareheldintheconsolidatedbalancesheetatcostlessamortizationandimpairment.Amortizationappliesonastraight-linebasisinrespect

ofassetshavingafiniteestimatedusefuleconomiclife.TheCompanyperformsaqualitativeassessmentannuallytodeterminewhetheritismorelikelythannotthatanintangibleassetconsideredtohaveanindefinitelifeisimpaired.Goodwillisassessedannuallyforimpairmentormorefrequentlyifcircumstancesindicateanimpairmentmayhaveoccurred.

(f)Accounting for Office Properties and EquipmentOfficeproperties andequipment are carriedat cost less accumulateddepreciation. Theseassets are depreciatedonastraight-line basis overtheestimated

usefullivesoftheassets.Computerequipmentandsoftwareisdepreciatedbetweenthreeandfiveyearswithdepreciationforsoftwarecommencingonthedatethesoftwareisbroughtintouse.Furnitureandfittingsaredepreciatedoverfouryearsandleaseholdimprovementsaredepreciatedoverthelesserof15yearsortheleaseterm.

(g)Accounting for Right-of-Use Operating Lease AssetsRight-of-useoperatingleaseassetscompriseprimarilyofleasedofficerealestateandotherassets.Forallofficerealestateleases,rentincentives,including

reduced-rentandrentfreeperiodsandcontractuallyagreedrentincreasesduringtheleaseterm,havebeenincludedwhendeterminingthepresentvalueoffuturecashflows.Right-of-useoperatingleaseassetsarecarriedatcostlessaccumulateddepreciation.Right-of-useoperatingleaseassetsaredepreciatedovertheleaseterm.

Right-of-useoperatingleaseassets are testedfor impairments whenever events or changesincircumstances indicate that thecarryingamount maynot berecoverable.Ifthecarryingvalueofanassetisimpaired,itisreducedtotherecoverableamountbyanimmediatechargetotheincomestatement.Therecoverableamountisthehigherofanasset’sfairvaluelesscoststosellandvalueinuse.

(h)Accounting for Foreign Currencies TranslationThereportingcurrencyoftheCompanyistheU.S.Dollar.ThefunctionalcurrenciesoftheCompany’sforeignoperationsandbranchesarethecurrenciesin

whichthemajorityoftheirbusinessistransacted.Transactionsincurrenciesotherthanthefunctionalcurrencyaremeasuredinthefunctionalcurrencyofthatoperationattheexchangerateprevailingatthe

dateofthetransaction.Monetaryassetsandliabilitiesdenominatedinnon-functionalcurrenciesareremeasuredattheexchangerateprevailingatthebalancesheetdateandanyresultingforeignexchangegainsorlossesarereflectedinthestatementofoperations.

Monetary and non-monetary assets and liabilities of the Company’s functional currency operations are translated into U.S. Dollars at the exchange rateprevailingatthebalancesheetdate.Incomeandexpensesoftheseoperationsaretranslatedattheexchangerateprevailingatthedateofthetransaction.Unrealizedgainsorlossesarisingfromthetranslationoffunctionalcurrenciesarerecordednetoftaxasacomponentofothercomprehensiveincome.

(i)Accounting for Income TaxesIncome taxes are accounted for under the asset and liability method. Deferred tax assets and liabilities are recognized for the future tax consequences

attributabletodifferencesbetweenthefinancialstatementcarryingamountsofexistingassetsandliabilitiesandtheirrespectivetaxbasesandforoperatinglossandtaxcredit carryforwards. Deferredtaxassets andliabilities aremeasuredusingenactedtaxratesexpectedtoapplytotaxableincomeintheyears inwhichthosetemporarydifferencesareexpectedtoberecoveredorsettled. WhentheCompanydoesnotbelievethat, onthebasis ofavailable information, it is morelikelythannotthatdeferredtaxassetswillbefullyrecovered,itrecognizesavaluationallowanceagainstitsdeferredtaxassetstoreducethedeferredtaxassetstotheamountmorelikelythannottoberealized.Theeffectondeferredtaxassetsandliabilitiesofachangeintaxratesisrecognizedinincomeintheperiodthatincludestheenactmentdate.

Furthermore,ataxbenefitfromataxpositionmayberecognizedinthefinancialstatementsonlyifitismore-likely-than-notthatthepositionissustainable,basedsolelyonits technical merits andconsiderationoftherelevant taxauthority’s widelyunderstoodadministrative practices andprecedents. Thetaxbenefitrecognized,whenthelikelihoodofrealizationismorelikely-than-not(i.e.greaterthan50percent),ismeasuredatthelargestamountthatisgreaterthan50percentlikelyofbeingrealizeduponsettlement.

TheCompanyappliesaportfolioapproachtoreleasetheincometaxeffectsinaccumulatedothercomprehensiveincome.Underthisapproach,theincometax effects uponthe sale of an available-for-sale debt security, settlement of hedgedtransactions anduponforeign currency translation adjustments as of eachperiodend,aredeterminedundertheintraperiodtaxallocationapproach.Anytaxeffectsremaininginaccumulatedothercomprehensiveincomeareonlyreleasedwhentheentireportfolioisliquidated,soldorextinguished.

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(j)Accounting for Preference SharesTheCompanyhadatthebalancesheetdateinissuethreeclassesofpreferenceshares.TheCompanyhasnoobligationtopayinterestonthesesecuritiesbut

they carry entitlements to dividends payable at the discretion of the Board of Directors. In the event of non-payment of dividends for six consecutive periods,holdersofpreferenceshareshavedirectorappointmentrights.Thepreferencesharesarethereforeaccountedforasequityinstrumentsandincludedwithintotalshareholders’equity.

(k)Accounting for Long-Term Incentive PlansThe Company operates an employee long-term incentive plan, comprised of Performance Units and Exit Units, the terms and conditions of which are

described in Note 16. The Company applies a fair-value based measurement method in calculating the compensation costs of Performance Units which arerecognizedonastraightlinebasisoverthevestingperiod.

PriortotheMerger,theCompanyoperatedanemployeeshareincentiveplan,anon-executivedirectorstockincentiveplanandemployeesharepurchaseplans,thetermsandconditionsofwhicharedescribedinNote16.TheCompanyappliedafair-valuebasedmeasurementmethodincludingestimatesforfutureforfeituresinthecalculationofthecompensationcostsofstockoptions,performanceshares,phantomsharesandrestrictedshareunits.(l) Accounting for Long-Term Debt Issued by Variable Interest Entities

Silverton, a previously consolidated variable interest entity, issued debt instruments as further described in Note 5, “Variable Interest Entities” of theseconsolidatedfinancialstatements.ThisdebtwasseparatelyidentifiedontheCompany’sbalancesheetandtheCompanyelectedtorecordthedebtatfairvalueduetothepotentialvariabilityovertheultimatesettlementvalueofthedebtinstruments.

(m) Accounting for Business CombinationsTheCompanyaccounts for a transactionasa business combinationwheretheassets acquiredandliabilities assumedfollowingatransactionconstitute a

business. Anacquiredentitymusthaveinputsandprocessesthatmakeit capableofgeneratingareturnoreconomicbenefit tobeconsideredabusiness.If theassetsacquiredarenotabusiness,theCompanyaccountsthetransactionasanassetacquisition.TheCompanyrecognizesandmeasuresatfairvalue100percentoftheassetsandliabilitiesofanyacquiredbusiness.Goodwillisrecognizedandmeasuredasthedifferencebetweentheconsiderationpaidorpayablelessthefairvalueofassetsacquired.

TheCompanyaccountsforthedisposalofsubsidiaryundertakingswhenitceasestocontrolthesubsidiary’sassetsandliabilitiesorthegroupofassets.Again or loss is recognized andmeasured as the difference betweenthe fair value of consideration received or receivable andthe value of assets, liabilities andequitycomponentsde-recognized,relatedtothatsubsidiaryorgroupofassetswhendeconsolidated.

Coststhataredirectlyrelatedtoabusinesscombinationtransactionareexpensedintheperiodsinwiththecostsareincurredandtheservicesarereceived.

(n) Accounting Pronouncements

Accounting Pronouncements Adopted in 2020

OnJune 16, 2016, the Financial Accounting Standards Board (the “FASB”) issued ASU2016-13, “Financial Instruments - Credit Losses (Topic 326)”whichintroducedanewimpairmentmodel,knownasthecurrentexpectedcreditlossmodel,whichisbasedonexpectedlossesratherthanincurredlosses.Underthenewcredit lossmodel, theCompanywouldrecognizeanallowanceforitsestimateofexpectedcredit lossesandthiswouldapplytomostdebtinstruments(otherthanthosemeasuredatfairvalue),tradereceivables,leasereceivables,reinsurancereceivables,financialguaranteecontractsandloancommitments.ThisASUalsomadelimitedamendmentstotheimpairmentmodelforavailable-for-saledebtsecurities,requiringanallowanceforcreditlossestoberecognized.TherewereotheramendmentsrequiredasaresultofthisASUthatareeffectiveforfiscalyearsbeginningafterDecember15,2019.Additionally,onMay15,2019,theFASBissuedASU2019-05,“Financial Instruments - Credit Losses (Topic 326)” whichallowedanentity,uponadoptionofASU2016-13,toirrevocablyelectthefair value option on an instrument-by-instrument basis (except for existing held-to-maturity securities). If an entity elects the fair value option, the differencebetweentheinstrument’sfairvalueandcarryingamountisrecognizedasacumulative-effectadjustment.ThisASUiseffectiveforfiscalyearsbeginningafterDecember15,2019andinterimperiodswithinthosefiscalyears.FollowingtheadoptionoftheseASUswitheffectfromJanuary1,2020,theCompanyrecognizedareductionintheCompany’savailable-for-saleinvestmentportfolioandreinsurancerecoverablesby$0.6millionand$3.7million,respectively,

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asaresultofrecognizingcurrentexpectedcreditlosses(“CECL”),togetherwithacumulativeeffectadjustmentof$4.3millionthroughopeningretainedearnings.On October 31, 2018, the FASB issued ASU 2018-17, “Consolidation (Topic 810)” which makes targeted improvements to related party guidance for

variableinterest entities, requiringthereportingentitytoconsiderindirect interests heldthroughrelatedparties undercommoncontrol onaproportionatebasiswhenevaluatingwhetheradecision-maker’sfeeisavariableinterestforpurposesoftheprimarybeneficiarytest.TheamendmentsofthisASUareeffectiveforfiscal years beginning after December 15, 2019 and interim periods within those fiscal years. Adoption of this ASU did not have a material impact on theCompany’sfinancialstatementsanddisclosures.

OnApril4,2019,theFASBissuedASU2019-04,“Codification Improvements to Topic 326, Financial Instruments - Credit Losses, Topic 815, Derivativesand Hedging, and Topic 825, Financial Instruments” amending guidance on credit losses, hedging, and recognizing and measuring financial instruments inresponse to questions raised by stakeholders and to correct unintended application. The amendments of this ASUare effective for fiscal years beginning afterDecember15,2019andinterimperiodswithinthosefiscalyearsforbothTopic326andTopic825,whereasforTopic815theamendmentsareeffectiveasofthebeginningoftheentity’snextannualperiodforentitiesthathavealreadyadoptedthehedgeaccountingstandard.AdoptionofthisASUdidnothaveamaterialimpactontheCompany’sfinancialstatementsanddisclosures.

OnMarch12,2020,theFASBissuedASU2020-04,“Reference Date Reform (Topic 848)”whichprovidesoptionalguidanceforalimitedperiodoftime(March12,2020toDecember31,2022)aimingateasingthepotentialburdeninaccountingfortheeffectsofreferenceratereform,suchasthepotentialcessationoftheLondonInterbankOfferedRate(“LIBOR”).ThisASUiseffectiveasofMarch12,2020throughDecember31,2022.AdoptionofthisASUdidnothaveamaterialimpactontheCompany’sfinancialstatementsanddisclosures.

Accounting Pronouncements Not Yet AdoptedOnDecember18,2019,theFASBissuedASU2019-12,“Income Taxes (Topic 740)”whichmakesamendmentsaimedatsimplifyingtheaccountingfor

incometaxes.ThisASUwillbeeffectiveforfiscalyearsbeginningafterDecember15,2020andinterimperiodswithinthosefiscalyears.Duringtheyear,theCompanyevaluatedandconsideredtheprovisionsofASU2019-12andhasconcludedthatthereisnomaterialimpactontheconsolidatedfinancialstatementsforthecurrentandfuturefinancialyears.

OtheraccountingpronouncementswereissuedduringtheyearendedDecember31,2020whichwereeithernotrelevanttotheCompanyordidnotimpacttheCompany’sconsolidatedfinancialstatements.

3. Segment ReportingThe Company is organized into two business segments, namely Aspen Re and Aspen Insurance. The Company has determined its reportable segments,

AspenRe(“Reinsurance”)andAspenInsurance(“Insurance”),bytakingintoaccountthemannerinwhichmanagementmakesoperatingdecisionsandassessesoperatingperformance.ProfitorlossforeachoftheCompany’sbusinesssegmentsismeasuredbyunderwritingprofitorloss.Underwritingprofitistheexcessofnet earned premiums over the sum of losses and loss expenses, amortization of deferred policy acquisition costs and general and administrative expenses.Underwritingprofitorlossprovidesabasisformanagementtoevaluatethesegment’sunderwritingperformance.

Reinsurance Segment.Thereinsurancesegmentconsistsofpropertycatastrophereinsurance,otherpropertyreinsurance,casualtyreinsuranceandspecialtyreinsurance.AspenCapitalMarketsfocusesondevelopingalternativereinsurancestructurestoleveragetheCompany’sexistingunderwritingfranchise,increaseitsoperationalflexibilityinthecapitalmarketsandprovideinvestorsdirectaccesstoitsunderwritingexpertise.AspenCapitalMarketsleveragestheCompany’sunderwritingandanalyticalexpertiseandearnsmanagementandperformancefeesfromthird-partyinvestorsprimarilythroughthemanagementofILSfundsandother offerings. For a more detailed description of this business segment, refer to Item 4, “Information on the Company — Business Overview — AspenReinsurance”above.

Insurance Segment.Theinsurancesegmentconsistsofpropertyandcasualtyinsurance,marine,aviationandenergyinsuranceandfinancialandprofessionallinesinsurance.Foramoredetaileddescriptionofthissegment,refertoItem4“InformationontheCompany—BusinessOverview—AspenInsurance”above.

Non-underwriting Disclosures.TheCompanyprovidesadditionaldisclosuresforcorporateandother(non-operating)incomeandexpenses.Corporateandotherincomeandexpensesincludenetinvestmentincome,netrealizedandunrealizedinvestmentgainsorlosses,expensesassociatedwithmanagingtheAspenGroup,certainstrategicandothercosts,changesinfairvalueofderivativesortheloannotesissuedbyvariableinterestentities,interestexpenses,netrealizedandunrealizedforeignexchangegainsorlosses,assetimpairmentsandincometaxes,noneofwhichareallocatedtothebusinesssegments.ThesecorporateexpensesarenotallocatedtotheCompany’sbusinesssegmentsastheyarenotdirectlyrelatedtotheCompany’sbusinesssegmentoperationsandisconsistentwithhowmanagementmeasurestheperformanceofitssegments.

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The Companydoes not allocate its assets by business segment as it evaluates underwriting results of each business segment separately fromthe results of theCompany’sinvestmentportfolio.

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The Company uses underwriting ratios as measures of performance. The loss ratio is the ratio of losses and loss adjustment expenses to net earnedpremiums. The policy acquisition expense ratio is the ratio of amortization of deferred policy acquisition costs to net earned premiums. The general andadministrativeexpenseratioistheratioofgeneral,administrativeandcorporateexpensestonetearnedpremiums.Thecombinedratioisthesumofthelossratio,thepolicyacquisitionexpenseratioandthegeneralandadministrativeexpenseratio.

Thefollowingtablesprovideasummaryofgrossandnetwrittenandearnedpremiums,underwritingresults,ratiosandreservesforeachoftheCompany’sbusinesssegmentsforthetwelvemonthsendedDecember31,2020,2019and2018: Twelve Months Ended December 31, 2020 Reinsurance Insurance Total ($ in millions)Underwriting RevenuesGrosswrittenpremiums $ 1,660.8 $ 2,042.8 $ 3,703.6Netwrittenpremiums 1,302.1 1,280.8 2,582.9Grossearnedpremiums 1,616.4 2,027.1 3,643.5Netearnedpremiums 1,292.1 1,240.5 2,532.6Underwriting ExpensesLossesandlossadjustmentexpenses 958.6 882.2 1,840.8Amortizationofdeferredpolicyacquisitioncosts 246.0 219.7 465.7Generalandadministrativeexpenses 110.8 197.2 308.0Underwriting(loss) (23.3) (58.6) (81.9)Corporateexpenses (70.2)Non-operatingexpenses (32.7)Netinvestmentincome 154.6Realizedandunrealizedinvestmentgains 98.5Realizedandunrealizedinvestmentlosses (27.4)Changeinfairvalueofderivatives (65.1)Interestexpenseonlongtermdebt (33.9)Netrealizedandunrealizedforeignexchange(losses) (12.4)Otherincome 49.8Otherexpenses (10.8)(Loss)beforeincometaxes (31.5)Incometax(expense) (8.6)Net(loss) $ (40.1)

Netreservesforlossandlossadjustmentexpenses $ 2,095.7 $ 1,874.4 $ 3,970.1RatiosLossratio 74.2% 71.1% 72.7%

Policyacquisitionexpenseratio 19.0 17.7 18.4Generalandadministrativeexpenseratio 8.6 15.9 16.2

Expenseratio 27.6 33.6 34.6Combinedratio 101.8% 104.7% 107.3%

_______________Non-operatingexpensesincludes$18.2millionofcostsrelatedtoseverance,retentionawardsandothercosts,$12.9millionofimpairmentchargesrelatedtoleaseassetsasaresultofsub-leasingcertainofficespaceand$1.6millionofamortizationofintangibleassetsandothernon-operatingexpenses.Includesthegainonsaleofourrenewalrightsonoursuretyinsurancebookofbusinesstoathirdparty,totaling$43.1million.Thegeneralandadministrativeexpenseratiointhetotalcolumnincludescorporateandnon-operatingexpenses.

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Twelve Months Ended December 31, 2019 Reinsurance Insurance Total ( $ in millions)Underwriting RevenuesGrosswrittenpremiums $ 1,485.5 $ 1,956.9 $ 3,442.4Netwrittenpremiums 1,251.1 1,176.8 2,427.9Grossearnedpremiums 1,494.9 1,927.5 3,422.4Netearnedpremiums 1,255.2 1,038.1 2,293.3Underwriting ExpensesLossesandlossadjustmentexpenses 917.9 761.8 1,679.7Amortizationofdeferredpolicyacquisitioncosts 264.9 147.8 412.7Generalandadministrativeexpenses 111.7 229.8 341.5Underwriting(loss) (39.3) (101.3) (140.6)Corporateexpenses (54.5)Non-operatingexpenses (125.6)Netinvestmentincome 197.3Realizedandunrealizedinvestmentgains 97.1Realizedandunrealizedinvestmentlosses (10.9)Realizedlossondebtextinguishment (5.5)Changeinfairvalueofloannotesissuedbyvariableinterestentities (3.1)Changeinfairvalueofderivatives (144.2)Interestexpenseonlongtermdebt (20.2)Netrealizedandunrealizedforeignexchange(losses) (11.8)Otherincome 4.9Otherexpenses (1.7)(Loss)beforeincometaxes (218.8)Incometax(expense) (22.9)Net(loss) $ (241.7)

Netreservesforlossandlossadjustmentexpenses $ 2,605.9 $ 2,026.1 $ 4,632.0RatiosLossratio 73.1% 73.4% 73.2%

Policyacquisitionexpenseratio 21.1 14.2 18.0Generalandadministrativeexpenseratio 8.9 22.1 22.7

Expenseratio 30.0 36.3 40.7Combinedratio 103.1% 109.7% 113.9%

________________

Non-operatingexpensesincludes$103.4millionofcostsrelatedtotheMerger,severance,retentionandothercosts,$22.2millionofexpensesrelatedtotheCompany’soperatingeffectivenessandefficiencyprogram,whichincludes$12.3millionofimpairmentchargesrelatedtoleaseassetsasaresultofsub-leasingcertainofficespace.Thegeneralandadministrativeexpenseratiointhetotalcolumnincludescorporateandnon-operatingexpenses.

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Twelve Months Ended December 31, 2018 Reinsurance Insurance Total ($ in millions)Underwriting RevenuesGrosswrittenpremiums $ 1,495.7 $ 1,951.2 $ 3,446.9Netwrittenpremiums 1,182.9 899.1 2,082.0Grossearnedpremiums 1,593.9 1,940.5 3,534.4Netearnedpremiums 1,256.4 958.3 2,214.7Underwriting ExpensesLossesandlossadjustmentexpenses 927.0 646.0 1,573.0Amortizationofdeferredpolicyacquisitioncosts 260.9 110.7 371.6Generalandadministrativeexpenses 118.5 239.2 357.7Underwriting(loss) (50.0) (37.6) (87.6)Corporateexpenses (56.8)Non-operatingexpenses (77.2)Netinvestmentincome 198.2Realizedandunrealizedinvestmentgains 110.0Realizedandunrealizedinvestmentlosses (174.7)Realized(loss)ondebtextinguishment (8.6)Changeinfairvalueofloannotesissuedbyvariableinterestentities (4.4)Changeinfairvalueofderivatives (31.8)Interestexpenseonlongtermdebt (25.9)Netrealizedandunrealizedforeignexchange(losses) (3.5)Otherincome 9.0Otherexpenses (2.7)(Loss)beforeincometaxes (156.0)Incometaxbenefit 10.2Net(loss) $ (145.8)

Netreservesforlossandlossadjustmentexpenses $ 2,843.6 $ 2,153.0 $ 4,996.6RatiosLossratio 73.8% 67.4% 71.0%

Policyacquisitionexpenseratio 20.8 11.6 16.8Generalandadministrativeexpenseratio 9.4 25.0 22.2

Expenseratio 30.2 36.6 39.0Combinedratio 104.0% 104.0% 110.0%

_______________Non-operatingexpensesincludes$37.5millionofexpensesrelatedtoCompany’soperatingeffectivenessandefficiencyprogram,$39.0millionofadvisorfeesrelatedtotheMergerand$11.3millionofretentioncosts,partiallyoffsetbythewritebackofa$14.1millionbuy-outprovision.Thegeneralandadministrativeexpenseratiointhetotalcolumnincludescorporateandnon-operatingexpenses.

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Geographical Areas.ThefollowingsummarypresentstheCompany’sgrosswrittenpremiumsbasedonthelocationoftheinsuredriskforthetwelvemonthsendedDecember31,2020,2019and2018.

For the Twelve Months Ended December 31, 2020 December 31, 2019 December 31, 2018 ($ in millions)Australia/Asia $ 259.7 $ 215.9 $ 175.9Caribbean 6.0 9.3 7.7Europe 92.5 82.8 92.6UnitedKingdom 374.1 295.7 290.1UnitedStates&Canada 2,267.5 2,003.9 1,875.9WorldwideexcludingUnitedStates 23.1 63.0 70.1WorldwideincludingUnitedStates 501.2 614.9 775.8Others 179.5 156.9 158.8Total $ 3,703.6 $ 3,442.4 $ 3,446.9

______________“UnitedStatesandCanada”comprisesindividualpoliciesthatinsurerisksspecificallyintheUnitedStatesand/orCanada,butnotelsewhere.“WorldwideexcludingtheUnitedStates”comprisesindividualpoliciesthatinsureriskswherevertheymaybeacrosstheworldbutspecificallyexcludesthe

UnitedStates.“WorldwideincludingtheUnitedStates”comprisesindividualpoliciesthatinsureriskswherevertheymaybeacrosstheworldbutspecificallyincludesthe

UnitedStates.

4. InvestmentsIncome Statement

Investment Income.ThefollowingtablesummarizesinvestmentincomeforthetwelvemonthsendedDecember31,2020,2019and2018:For the Twelve Months Ended

December 31, 2020 December 31, 2019 December 31, 2018 ($ in millions)Fixedincomesecurities—Availableforsale $ 106.5 $ 128.2 $ 134.1Fixedincomesecurities—Trading 32.8 42.0 49.6Short-terminvestments—Availableforsale 0.8 2.3 1.4Short-terminvestments—Trading 0.5 2.5 0.4Fixedtermdeposits(includedincashandcashequivalents) 6.4 19.5 14.2Equitysecurities—Trading — — 2.1Catastrophebonds—Trading 1.4 2.3 2.8Privately-heldinvestments—Trading 20.9 3.4 —Otherinvestments,atfairvalue (2.0) 8.9 2.5Total 167.3 209.1 207.1Investmentexpenses (12.7) (11.8) (8.9)Netinvestmentincome $ 154.6 $ 197.3 $ 198.2

______________OtherinvestmentsrepresentstheCompany’sinvestmentinarealestatefund.Themovementintheyearrepresentsthechangeinfairvalueoftheinvestment

andhasbeenincludedaspartofourinvestmentincome.

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The following table summarizes the net realized and unrealized investment gains and losses recorded in the statement of operations and the change inunrealizedgainsandlossesoninvestmentsrecordedinothercomprehensiveincomeforthetwelvemonthsendedDecember31,2020,2019and2018:

For the Twelve Months EndedDecember 31, 2020 December 31, 2019 December 31, 2018

($ in millions)Availableforsale:

Fixedincomesecurities—grossrealizedgains $ 68.8 $ 14.4 $ 6.4Fixedincomesecurities—grossrealized(losses) (1.8) (7.3) (11.4)Cashandcashequivalents—grossrealizedgains 0.5 0.1 0.3Cashandcashequivalents—grossrealized(losses) (0.4) (0.2) (0.5)Netchangeinexpectedcreditgains 0.4 — —

Trading:Fixedincomesecurities—grossrealizedgains 18.2 34.3 4.6Fixedincomesecurities—grossrealized(losses) (3.8) (2.6) (25.0)Short-terminvestments—grossrealizedgains — — 0.1Short-terminvestments—grossrealized(losses) — — (4.2)Cashandcashequivalents—grossrealizedgains 0.2 — 1.5Cashandcashequivalents—grossrealized(losses) (0.3) (0.3) (0.3)Equitysecurities—grossrealizedgains — — 94.5Equitysecurities—grossrealized(losses) — — (20.1)Privately-heldinvestments—grossrealizedgains — 0.2 —Privately-heldinvestments—grossrealized(losses) — (0.2) —Privately-heldinvestments—netchangeingrossunrealized(losses) (20.4) — —Catastrophebonds—netunrealizedgains — 0.9 2.2Netchangeingrossunrealizedgains/(losses) — 47.2 (112.1)

Investments—equitymethod:Grossrealizedandunrealized(loss)inMVI (0.4) (0.1) (0.2)Grossrealizedandunrealized(loss)gaininDigitalRisk (0.3) (0.2) 0.4GrossrealizedandunrealizedgaininBene — — (0.9)GrossrealizedgainonsaleofBene 1.8 — —GrossrealizedgainonsaleofCropRe 8.6 — —Totalnetrealizedandunrealizedinvestmentgains/(losses)recordedinthestatementofoperations $ 71.1 $ 86.2 $ (64.7)

Changeinavailableforsalenetunrealizedgain/(losses):Fixedincomesecurities 108.5 164.9 (81.3)

Incometax(expense)/benefit (6.2) (13.6) 4.8Totalchangeinnetunrealizedgains/(losses),netoftaxesrecordedinothercomprehensiveincome $ 102.3 $ 151.3 $ (76.5)

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Balance SheetFixed Income Securities and Short-Term Investments — Available For Sale.Thefollowingtablespresentthecostoramortizedcost,grossunrealizedgains

andlossesandestimatedfairmarketvalueofavailableforsaleinvestmentsinfixedincomesecuritiesandshort-terminvestmentsasatDecember31,2020andDecember31,2019: As at December 31, 2020

Cost or

Amortized Cost

Gross Unrealized

Gains

Gross Unrealized

LossesAllowance forCredit Losses

Fair Market Value

($ in millions)U.S.government $ 1,041.3 $ 60.5 $ (0.6) $ — $ 1,101.2U.S.agency 32.8 1.5 — — 34.3Municipal 61.6 5.5 — — 67.1Corporate 1,714.5 112.0 (0.1) (0.2) 1,826.2Non-U.S.government-backedcorporate 62.7 0.7 — — 63.4Non-U.S.government 268.8 4.3 — — 273.1Asset-backed 2.3 — — — 2.3Non-agencycommercialmortgage-backed 6.7 0.7 — — 7.4Agencymortgage-backed 936.0 37.2 (0.1) — 973.1Totalfixedincomesecurities—Availableforsale 4,126.7 222.4 (0.8) (0.2) 4,348.1Totalshort-terminvestments—Availableforsale 88.0 — (0.2) — 87.8Total $ 4,214.7 $ 222.4 $ (1.0) $ (0.2) $ 4,435.9

EffectiveJanuary1,2020,theCompanyadoptedASU2016-13prospectivelyandasaresultanycreditlossesontheCompany'savailable-for-saleinvestmentsarerecordedasanallowance,subjecttoreversal.SeeNote2,“BasisofPreparationandSignificantAccountingPolicies”andNote23,“AllowanceforCreditLosses”forfurtherdetails.

As at December 31, 2019

Cost or

Amortized Cost

Gross Unrealized

Gains

Gross Unrealized

LossesFair Market

Value ($ in millions)U.S.government $ 1,383.2 $ 31.3 $ (1.4) $ 1,413.1U.S.agency 38.7 0.9 — 39.6Municipal 47.8 2.9 — 50.7Corporate 1,905.6 54.8 (0.6) 1,959.8Non-U.S.government-backedcorporate 86.1 0.5 (0.1) 86.5Non-U.S.government 324.7 4.5 (0.4) 328.8Asset-backed 0.2 — — 0.2Non-agencycommercialmortgage-backed 6.7 — (0.2) 6.5Agencymortgage-backed 1,052.2 21.9 (1.1) 1,073.0Totalfixedincomesecurities—Availableforsale 4,845.2 116.8 (3.8) 4,958.2Totalshort-terminvestments—Availableforsale 117.6 — — 117.6Total $ 4,962.8 $ 116.8 $ (3.8) $ 5,075.8

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Fixed Income Securities, Short Term Investments, Equities, Catastrophe Bonds and Privately-held Investments — Trading.Thefollowingtablespresentthecostoramortizedcost,grossunrealizedgainsandlosses,andestimatedfairmarketvalueoftradinginvestmentsinfixedincomesecurities,short-terminvestments,equitysecurities,catastrophebondsandprivately-heldinvestmentsasatDecember31,2020andDecember31,2019: As at December 31, 2020

Cost or

Amortized Cost

Gross Unrealized

Gains

Gross Unrealized

LossesFair Market

Value ($ in millions)FixedIncomeSecurities—Trading

U.S.government $ 117.9 $ 2.7 $ (0.1) $ 120.5Municipal 3.2 0.3 — 3.5Corporate 94.4 9.1 — 103.5Highyieldloans 10.0 — (0.2) 9.8Non-U.S.government 41.5 0.1 — 41.6Asset-backed 541.7 3.1 (5.7) 539.1Agencymortgage-backed 36.1 1.5 — 37.6

Totalfixedincomesecurities—Trading 844.8 16.8 (6.0) 855.6Short-terminvestments—Trading 35.4 — — 35.4Catastrophebonds—Trading 18.8 — — 18.8Privately-heldinvestments—Trading

Commercialmortgageloans $ 178.6 $ 0.1 $ (15.1) $ 163.6Middlemarketloans 117.4 0.2 (5.5) 112.1Asset-backedsecurities 18.7 — (0.1) 18.6Equitysecurities 5.0 — — 5.0

Totalprivately-heldinvestments—Trading 319.7 0.3 (20.7) 299.3TotalInvestments—Trading $ 1,218.7 $ 17.1 $ (26.7) $ 1,209.1

As at December 31, 2019

Cost or

Amortized Cost

Gross Unrealized

Gains

Gross Unrealized

LossesFair Market

Value ($ in millions)FixedIncomeSecurities—Trading

U.S.government $ 183.3 $ 1.8 $ (0.1) $ 185.0Municipal 3.1 0.1 — 3.2Corporate 231.7 11.6 (0.1) 243.2Non-U.S.government 143.9 7.4 (0.1) 151.2Asset-backed 491.7 2.4 (1.7) 492.4Agencymortgage-backed 52.9 0.9 — 53.8

Totalfixedincomesecurities—Trading 1,106.6 24.2 (2.0) 1,128.8Short-terminvestments—Trading 79.2 — — 79.2Catastrophebonds—Trading 29.4 — (0.8) 28.6Privately-heldinvestments—Trading

Commercialmortgageloans 156.3 0.3 — 156.6Middlemarketloans 111.7 0.2 (0.2) 111.7Asset-backedsecurities 8.7 — — 8.7Equitysecurities 2.5 0.2 — 2.7

Totalprivately-heldinvestments—Trading 279.2 0.7 (0.2) 279.7TotalInvestments—Trading $ 1,494.4 $ 24.9 $ (3.0) $ 1,516.3

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The Company classifies the financial instruments listed above as held for trading because this most closely reflects the facts and circumstances of theinvestmentsheld.

AsatDecember31,2020,theCompanyhadnopositionsinU.S.DollarBBBEmergingMarketDebtanda1.5%positioninarealestatefundanda3.6%positioninMMLandCML,representingintotal5.1%ofourManagedPortfolio(December31,2019—8.2%).

Catastrophe bonds. TheCompanyhasinvestedincatastrophebondswithatotal valueof$18.8millionasat December31,2020(December31,2019—$28.6million).Thebondsareeitherzero-couponnotesorreceivequarterlyinterestpaymentsbasedonvariableinterestrateswithscheduledmaturitiesrangingfrom2019to2022.Theredemptionvalueofthebondswilladjustbasedontheoccurrenceoraggregateoccurrenceofacoveredevent,suchaswindstormsandearthquakesintheUnitedStates,Canada,theNorthAtlantic,SouthAmerica,Europe,JapanorAustralia.

Privately-held investments. TheCompanyhasinvestedinprivately-heldinvestments,whichprimarilyincludecommercialmortgageloansof$163.6millionandmiddlemarketloansof$112.1millionasatDecember31,2020(December31,2019—commercialmortgageloansof$156.6million;middlemarketloansof$111.7million).

Commercial Mortgage Loans. The commercial mortgage loans are related to investments in properties including apartments, hotels, office and retailbuildings,othercommercial propertiesandindustrial properties. Thecommercial mortgageloanportfolioisdiversifiedbypropertytype,geographicregionandissuertoreducerisks.Aspartofourinvestmentprocess,weevaluatefactorssuchassize,propertytype,andsecuritytodeterminethatpropertiesareperformingata consistent and acceptable level to secure the related debt. The following table presents the type of commercial mortgage loans and geographic region as atDecember31,2020andDecember31,2019:

As at December 31, 2020 As at December 31, 2019Net Carrying Value Percentage of Total Net Carrying Value Percentage of Total

($ millions) (%) ($ millions) (%)Property type

Apartment 80.7 49.3 48.3 30.8Hotels 20.4 12.5 47.7 30.4Officebuilding 33.9 20.7 21.9 14.0Othercommercial 28.6 17.5 17.0 10.9Retail — — 15.2 9.7Industrial — — 6.5 4.2Total commercial mortgage loans $ 163.6 100 % 156.6 100 %

Geographic RegionU.S. 122.7 75.0 85.5 54.6International 40.9 25.0 71.1 45.4Total commercial mortgage loans $ 163.6 100 % 156.6 100 %

Theprimarycreditqualityindicatorofcommercialmortgageloansisloanperformance.Non-performingcommercialmortgageloansaregenerally90daysormorepastdue.AsofDecember31,2020,$0.7millionofourcommercialmortgageloanswerenon-performing.Loan-to-valueanddebtservicecoverageratiosaremeasuresweusetoassesstheriskandqualityof commercial mortgageloans. Theloan-to-valueratiois expressedasapercentageof thevalueoftheloanrelativetothevalueoftheunderlyingproperty.Aloan-to-valueratioinexcessof100%indicatestheunpaidloanamountexceedstheunderlyingcollateral.Thefollowingtablerepresentstheloan-to-valueratioofthecommercialmortgageloanportfolioasatDecember31,2020andDecember31,2019:

As at December 31, 2020 As at December 31, 2019(in millions)

Lessthan50% $ 14.9 $ —50%to60% 39.3 80.561%to70% 99.5 35.571%to80% 9.9 40.6Commercial mortgage loans $ 163.6 $ 156.6

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Thedebt-servicecoverageratioismeasuredbyaproperty’snetoperatingincomeasamultipleofits debtre-payments. Aratiooflessthan1.0reflects aproperty’soperationsisnotsufficienttocoveritsdebtpayments.Thefollowingtablerepresentsthedebt-servicecoverageratioofthecommercialmortgageloanportfolio,excludingthosethatarenon-performingandconstructionloanswhicharestillunderdevelopment,asatDecember31,2020andDecember31,2019:

As at December 31, 2020 As at December 31, 2019(in millions)

Greaterthan1.20x $ 82.2 $ 94.61.00-1.20x 14.9 —Lessthan1.00x — 13.7Commercial mortgage loans 97.1 108.3

_______________ As at December 31, 2020, we have non-performing loans of $0.7 million (December 31, 2019 — $Nil) and construction loans of $65.8 million

(December31,2019—$48.4million)whichonlygenerateincomewhentheconstructioniscompleted.Asnoincomeiscurrentlybeinggeneratedontheseloans,theyarenotincludedinthetableabove.Thetotalvalueofcommercialmortgageloansare$163.6millionasatDecember31,2020,(December31,2019—$156.6million).Theprioryearnumbersinthetableabovehavebeenrepresentedtobeconsistentwiththecurrentyearpresentation.

Middle Market Loans.Themiddlemarketloansareinvestmentsinseniorsecuredloanpositionswithfullcovenants,focusedonthemiddlemarketinbothU.S.andEurope.Themiddlemarketloanportfolioisdiversifiedbyindustrytype,geographicregionandissuertoreducerisks.Aspartofourinvestmentprocess,weevaluatefactorssuchassize,industryandsecuritytodeterminethatloansareperformingataconsistentandacceptableleveltosecuretherelateddebt.ThefollowingtablepresentsthetypeofmiddlemarketloansandgeographicregionasatDecember31,2020andDecember31,2019:

As at December 31, 2020 As at December 31, 2019Net Carrying Value Percentage of Total Net Carrying Value Percentage of Total

($ millions) (%) ($ millions) (%)Industrytype

Materials 28.0 24.9 29.5 26.4Financials 27.1 24.2 22.2 19.8Industrials 17.3 15.5 18.9 17.0Consumerdiscretionary 13.7 12.2 14.2 12.7Healthcare 7.5 6.7 8.2 7.4Energy 7.3 6.5 7.4 6.6Consumerstaples 6.4 5.7 6.4 5.7Informationtechnology 4.8 4.3 4.9 4.4Totalmiddlemarketmortgageloans $ 112.1 100 % $ 111.7 100 %

GeographicRegionU.S. 91.8 81.9 91.8 82.2International 20.3 18.1 19.9 17.8Totalmiddlemarketloans $ 112.1 100 % $ 111.7 100 %

Theprimarycreditqualityindicatorofmiddlemarketloansisloanperformance.Non-performingmiddlemarketloansaregenerally90daysormorepastdue.AsofDecember31,2020,allofourmiddlemarketloanswereperforming.Loan-to-enterprise-valueandfixedchargecoverageratiosaremeasuresweusetoassesstheriskandqualityofmiddlemarketloans.Theloan-to-enterprise-valueratioisexpressedasapercentageofthevalueoftheloanrelativetothevalueofthebusiness.Aloan-to-enterprise-valueratioinexcessof100%indicatestheunpaidloanamountexceedsthevalueoftheunderlyingbusiness.Thefollowingtablerepresentstheloan-to-enterprise-valueratioofthemiddlemarketloanportfolioasatDecember31,2020andDecember31,2019:

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As at December 31, 2020 As at December 31, 2019(in millions)

Lessthan50% $ 59.8 $ 90.650%to60% 11.0 21.161%to70% 6.4 —81%to100% 17.2 —Greaterthan100% 17.7 —Middle market loans $ 112.1 $ 111.7

Thefixedchargecoverageratio,baseduponthemostrecentfinancialstatements,isexpressedasapercentageofafirm’searningsplusfixedchargestoitsfixed charges. Fixed charges include debt repayments, interest and equipment lease expenses. Afixed charge coverage ratio of less than 1.0 indicates a firm’soperationsdonotgenerateenoughincometocoveritsfixedcharges.ThefollowingrepresentsthefixedchargecoverageratioofthemiddlemarketloanportfolioasatDecember31,2020andDecember31,2019

As at December 31, 2020 As at December 31, 2019(in millions)

Greaterthan1.20x $ 73.6 $ 68.41.00-1.20x — 25.5Lessthan1.00x 38.5 17.8Middle market loans $ 112.1 $ 111.7

Asset-backed securities. Ourasset-backedsecuritiesportfolioofprivately-heldinvestmentsconsistsofasinglenon-U.S.basedissuerthatissuesfixedratenotesthatarebackedbyfutureflowsfrominternationalcreditcardcompaniesandthissecurityisperforming.

Equity securities. Our equity securities portfolio of privately-held investments consists of a single non-U.S. basedissuer that is a special purpose vehicledesigned to grant a first lien right to the underlying senior notes within the structure. The underlying issuer is a financial services lender to middle marketcompaniesandthissecurityisperforming.

Investments — Equity Method. In January 2015, the Company, along with seven other insurance companies, established a micro-insurance ventureconsortiumandmicro-insurance incubator (“MVI”) domiciled in Bermuda. TheMVIis a social impact organization that provides micro-insurance products toassistglobalemergingconsumers.TheCompany’sinitialinvestmentintheMVIwas$0.8million.TheCompanymadeanadditionalinvestmentof$0.1millioninthe twelve months ended December 31, 2017 and a further investment of $0.2 million in the twelve months ended December 31, 2018. In March, 2021 theCompanycommittedanadditional$0.8millionequitycontributiontoMVIovera2yearperiod.

OnJuly26,2016,theCompanypurchasedthroughitswholly-ownedsubsidiary,AcornLimited(“Acorn”),a20.0%shareofBeneAssicurazioni(“Bene”),anItalian-basedmotorinsurerforatotalconsiderationof$3.3million.TheinvestmentwasaccountedforundertheequitymethodandadjustmentstothecarryingvalueofthisinvestmentweremadebasedontheCompany’sshareofcapital,includingshareofincomeandexpenses.TheCompanymadeadditionalinvestmentsof$1.2millionand$1.1million,inthetwelvemonthsendedDecember31,2018andDecember31,2019,respectively.

OnNovember20,2020,theCompanysolditsinvestmentinBenefor$6.1million,releasingagainof$1.8million.On January 1, 2017, the Company purchased through its wholly-owned subsidiary, Aspen U.S. Holdings, Inc. (“Aspen U.S. Holdings”), a 49%share of

DigitalRiskResources,LLC(“DigitalRe”),aU.S.-basedenterpriseengagedinthebusinessofdeveloping,marketingandservicingturnkeyinformationsecurityandprivacyliabilityinsuranceproductsforatotalconsiderationof$2.3million.TheinvestmentisaccountedforundertheequitymethodandadjustmentstothecarryingvalueofthisinvestmentaremadebasedontheCompany’sshareofcapital,includingshareofincomeandexpenses.

OnDecember18,2017,theCompanyacquiredthroughitswholly-ownedsubsidiary,AspenU.S.Holdings,a23.2%shareofCropReServicesLLC(“CropRe”),anewlyformedU.S.-basedsubsidiaryofCGBDiversifiedServices,Inc(“CGBDS”)inexchangeforthesaleofAGLogicHoldings,LLC(“AgriLogic”),theCompany’sU.S.cropinsurancebusiness.

On December 14, 2020, we completed the sale of our 23.2%interest in Crop Re to CGBDS(the “CGBSale”). The CGBSale has and will result in amaterialdiminutionofourU.S.agriculturalbusinessin2021andbeyond.AsapartoftheCGBSale,CGBDSpaidAAIC$71.1millionforitsownershipinterestinCropRe,aswellas$14.5milliontosettlelosscarryforwardsforthe2018and2019cropyears.Inaddition,AAICenteredintoacommutationagreementwithCGBDS(the“CommutationAgreement”),underwhichAAICpaid$2.2milliontoCGBDSasacommutationsettlementforthe2018and2019cropyears.TheCommutation Agreement does not cover the cropyears from2010to 2017or the 2020cropyear, therefore weremain exposedto reinsurance obligations andpotentialclaimsinregardstothoseyears.

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OnDecember23,2019,theCompanycommitted$5.0millionasanequityinvestmentintheholdingcompanyofamulti-linereinsurer.Thestrategyforthemulti-linereinsureristocombineadiversifiedreinsurancebusiness,focusedprimarilyonlong-tailedlinesofpropertyandcasualtybusinessand,potentiallytoalesserextent,lifebusiness,withadiversifiedinvestmentstrategy.OnDecember27,2019,theCompanyreceivedademandforaninitialcapitalcallof$0.2millionandpaidthecapitalonJanuary15,2020.Duringthecourseof2020,afurther$0.3millioncapitalwasinvestedinthemulti-linereinsurer.

ThetablebelowshowstheCompany’sinvestmentsinMVI,Multi-LineReinsurer,Bene,DigitalReandCropReforthetwelvemonthsendedDecember31,2020and2019:

MVIMulti-LineReinsurer Bene Digital Re Crop Re Total

($ in millions)OpeningundistributedvalueofinvestmentasatJanuary1,2020 $ 0.4 $ — $ 4.3 $ 0.7 $ 62.5 $ 67.9Investmentintheperiod — 0.5 — — — 0.5Unrealized(loss)forthetwelvemonthstoDecember31,2020 (0.4) — — (0.3) — (0.7)Gainondisposal — — 1.8 — 8.6 10.4Proceedsfromdisposal — — (6.1) — (71.1) (77.2)ClosingvalueofinvestmentasatDecember31,2020 $ — $ 0.5 $ — $ 0.4 $ — 0.9

OpeningundistributedvalueofinvestmentasatJanuary1,2019 $ 0.5 $ — $ 3.2 $ 0.9 $ 62.5 $ 67.1Investmentintheperiod — — 1.1 — — 1.1Unrealized(loss)forthetwelvemonthstoDecember31,2019 (0.1) — — (0.2) — (0.3)ClosingvalueofinvestmentasatDecember31,2019 $ 0.4 $ — $ 4.3 $ 0.7 $ 62.5 $ 67.9

Other Investments.OnDecember20,2017,theCompanycommitted$100.0millionasalimitedpartnertoarealestatefund.Theinvestmentobjectiveofthefundistoachieveattractiverisk-adjustedreturnsthroughtheacquisitionofincomeproducing,highqualityassetsingatewaycitieslocatedintheU.S.andCanadaintheoffice,retail,industrialandmultifamilysectorsoftherealestatemarket.OnMay1,2018,theCompanyreceivedademandforaninitialcapitalcallof$86.2millionandpaidthecapitalcallonMay10,2018.OnSeptember19,2018,theCompanyreceivedademandforthefinalcapitalcallof$13.8millionandpaidthecapitalonSeptember28,2018.AsatDecember31,2020,thecurrentfairvalueoftherealestatefundis$109.4million.

Forfurtherinformationontherealestatefund,refertoNote20(a)intheseconsolidatedfinancialstatements,“CommitmentsandContingencies.”

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Fixed Income Securities. The scheduled maturity distribution of the Company’s available for sale fixed income securities as at December 31, 2020 andDecember31,2019issetforthbelow.Actualmaturitiesmaydifferfromcontractualmaturitiesbecauseissuersofsecuritiesmayhavetherighttocallorprepayobligationswithorwithoutcallorprepaymentpenalties. As at December 31, 2020

Amortized

Cost or CostFair Market

Value

Average S&P Ratings by

Maturity ($ in millions)Dueoneyearorless $ 498.6 $ 501.3 AADueafteroneyearthroughfiveyears 1,833.6 1,925.9 AA-Dueafterfiveyearsthroughtenyears 741.9 806.5 AA-Dueaftertenyears 107.6 131.6 AA-

Total—Governmentandcorporate 3,181.7 3,365.3Non-agencycommercialmortgage-backed 6.7 7.4 AA+Agencymortgage-backed 936.0 973.1 AA+Asset-backed 2.3 2.3 AAA

Totalfixedincomesecurities—Availableforsale $ 4,126.7 $ 4,348.1

At December 31, 2019

Amortized

Cost or CostFair Market

Value

Average S&P Ratings by

Maturity ($ in millions)Dueoneyearorless $ 572.7 $ 574.6 AADueafteroneyearthroughfiveyears 2,230.3 2,269.3 AA-Dueafterfiveyearsthroughtenyears 864.1 896.3 AA-Dueaftertenyears 119.0 138.3 AA-

Total—Governmentandcorporate 3,786.1 3,878.5Non-agencycommercialmortgage-backed 6.7 6.5 AA+Agencymortgage-backed 1,052.2 1,073.0 AA+Asset-backed 0.2 0.2 AAA

Totalfixedincomesecurities—Availableforsale $ 4,845.2 $ 4,958.2

Guaranteed Investments.AsatDecember31,2020andDecember31,2019,theCompanyheldnoinvestmentswhichareguaranteedbymono-lineinsurers,excludingthosewithexplicit governmentguarantees. TheCompany’sexposuretootherthird-partyguaranteeddebtis primarilytoinvestmentsbackedbynon-U.S.governmentguaranteedissuers.

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Gross Unrealized Losses. The following tables summarize, by type of security, the aggregate fair value and gross unrealized loss by length of time thesecurityhasbeeninanunrealizedlosspositionfortheCompany’savailableforsaleportfolioasatDecember31,2020andDecember31,2019: December 31, 2020 0-12 months Over 12 months Total

Fair Market Value

Gross Unrealized

Losses

Fair Market Value

Gross Unrealized

Losses

Fair Market Value

Gross Unrealized

LossesNumber of Securities

($ in millions)U.S.government $ 58.7 $ (0.6) $ — $ — $ 58.7 $ (0.6) 10Corporate 39.6 (0.1) — — 39.6 (0.1) 16Non-U.S.government 7.5 — — — 7.5 — 4Agencymortgage-backed 33.3 (0.1) 2.1 — 35.4 (0.1) 19

Totalfixedincomesecurities—Availableforsale 139.1 (0.8) 2.1 — 141.2 (0.8) 49Totalshort-terminvestments—Availableforsale 8.7 — — (0.2) 8.7 (0.2) 15Total $ 147.8 $ (0.8) $ 2.1 $ (0.2) $ 149.9 $ (1.0) 64

December 31, 2019 0-12 months Over 12 months Total

Fair Market Value

Gross Unrealized

Losses

Fair Market Value

Gross Unrealized

Losses

Fair Market Value

Gross Unrealized

LossesNumber of Securities

($ in millions)U.S.government $ 142.0 $ (1.0) $ 138.2 $ (0.4) $ 280.2 $ (1.4) 49U.S.agency 3.0 — 6.0 — 9.0 — 2Municipal 3.7 — — — 3.7 — 2Corporate 167.7 (0.6) 37.1 — 204.8 (0.6) 91Non-U.S.government-backedcorporate 31.8 (0.1) — — 31.8 (0.1) 9Non-U.S.government 48.6 (0.4) 0.6 — 49.2 (0.4) 20Asset-backed — — 0.2 — 0.2 — 1Non-agencycommercialmortgage-backedsecurities 6.5 (0.2) — — 6.5 (0.2) 1Agencymortgage-backed 149.7 (0.3) 68.4 (0.8) 218.1 (1.1) 80

Totalfixedincomesecurities—Availableforsale 553.0 (2.6) 250.5 (1.2) 803.5 (3.8) 255Totalshort-terminvestments—Availableforsale 29.5 — — — 29.5 — 5Total $ 582.5 $ (2.6) $ 250.5 $ (1.2) $ 833.0 $ (3.8) 260

Current Expected Credit Loss and Other-Than-Temporary Impairments.OnJune16,2016,theFASBissuedASU2016-13, “Financial Instruments - Credit Losses (Topic 326)”whichreplacedother-than-temporaryimpairment

(“OTTI”)byanewimpairmentmodel,knownasthecurrentexpectedlossmodel(“CECL”),whichisbasedonexpectedlossesratherthanincurredlosses.Foramore detailed description of accounting policies for CECLand OTTI, refer to Note 2(c), “Basis of Preparation and Significant Accounting Policies” of theseconsolidatedfinancialstatements.

CECL.FollowingtheadoptionofASU2016-13,witheffectfromJanuary1,2020,theCompanyrecognizedareductioninitsavailable-for-saleinvestmentportfoliototaling$0.6millionasaresultofrecognizingCECLthroughopeningretainedearningsforperiods2019andprior.

ForthetwelvemonthsendedDecember31,2020,therewasareductionintheCECLallowanceonavailable-for-saleinvestmentsof$0.4million.

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OTTI.Asecuritywaspotentiallyimpairedwhenitsfairvaluewasbelowitscostoramortizedcost.TheCompanyrevieweditsavailableforsalefixedincomeandequityportfoliosonanindividualsecuritybasisforpotentialOTTIeachquarterbasedoncriteriaincludingissuer-specificcircumstances,creditratingsactionsandgeneralmacro-economicconditions.ThetotalOTTIchargeforthetwelvemonthsendedDecember31,2019was$Nil.

5. Variable Interest EntitiesAsatDecember31,2020,theCompanyhadinvestmentsinone(December31,2019—one)variableinterestentity(“VIE”),namelyPeregrineReinsurance

Ltd(“Peregrine”).Peregrine.In November2016, Peregrine, a subsidiaryof theCompany, wasregisteredas a segregatedaccounts companyunder theSegregatedAccounts

Companies Act 2000, as amended. As at December 31, 2020, Peregrine had six segregated accounts which were funded by third-party investors and twosegregatedaccountswhicharefundedbyAspenareconsolidatedwithinthefinancialstatements.

TheCompanyhasdeterminedthatPeregrinehasthecharacteristicsofaVIEasaddressedbytheguidanceinASC810,Consolidation.Thesixsegregatedaccounts have not been consolidated as part of the Company’s consolidated financial statements because the Company is not the primary beneficiary of thoseaccounts.TheCompanyhas,however,concludedthatitistheprimarybeneficiaryofthePeregrinegeneralfundand,similartopriorreportingperiods,theresultsofthePeregrinegeneralfundareincludedintheCompany’sconsolidatedfinancialstatements.

Silverton. OnSeptember10,2013,theCompanyestablishedSilvertonReLtd(“Silverton”),aBermudadomiciledspecialpurposeinsurerformedtoprovideadditional collateralizedcapacitytosupport AspenRe’sbusinessthroughretrocessionagreementswhicharecollateralizedandfundedbySilvertonthroughtheissuanceofoneormoreseriesofparticipatingloannotes(collectively,the“LoanNotes”).Silvertonisanon-ratedinsurerandtherisksarefullycollateralizedbywayoffundsheldintrustforthebenefitofAspenBermudaandAspenU.K.,thecedingreinsurers.SilvertonhasnotissuedanyLoanNotessince2017.

AfinalpaymentwasmadetonoteholdersaftercommutationofthereinsuranceagreementonJuly1,2019.Silvertonhasnofurtherreinsurancecommitmentsoutstanding.

ThefollowingtablesshowthetotalliabilitybalanceoftheLoanNotesforthetwelvemonthsendedDecember31,2020and2019:

For the Twelve Months Ended December 31, 2020Third Party Aspen Holdings Total

($ in millions)Openingbalance $ — $ — $ —Totalchangeinfairvaluefortheperiod — — —Totaldistributedintheperiod — — —ClosingbalanceasatDecember31,2020 $ — $ — $ —

LiabilityLoannotes(long-termliabilities) $ — $ — $ —Accruedexpenses(currentliabilities) — — —TotalaggregateunpaidbalanceasatDecember31,2020 $ — $ — $ —

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For the Twelve Months Ended December 31, 2019Third Party Aspen Holdings Total

($ in millions)Openingbalance $ 4.6 $ 1.1 $ 5.7Totalchangeinfairvaluefortheperiod 3.1 0.8 3.9Totaldistributedintheperiod (7.7) (1.9) (9.6)ClosingbalanceasatDecember31,2019 $ — $ — $ —

LiabilityLoannotes(long-termliabilities) $ — $ — $ —Accruedexpenses(currentliabilities) — — —TotalaggregateunpaidbalanceasatDecember31,2019 $ — $ — $ —

TheCompanyhaddeterminedthatSilvertonhasthecharacteristicsofaVIEthatareaddressedbytheguidanceinASC810,Consolidation. TheCompanyconcluded that it was the primary beneficiary of Silverton as it ownedall of Silverton’s voting shares and issued share capital, and had a significant financialinterest in, and the power to control, Silverton. As a result, the Company consolidated Silverton upon its formation. The Company had no other obligation toprovidefinancialsupporttoSilvertonandneitherthecreditorsnorbeneficialinterestholdersofSilvertonhadrecoursetotheCompany’sgeneralcredit.

Aftercommutationofthe2017reinsurancecontractandsettlementofallLoanNotes,theCompanyhasdeterminedthatSilvertonwillnolongerberegardedasaVIE.

ForfurtherinformationregardingtheLoanNotesattributabletothethird-partyinvestmentsinSilverton,refertoNote6,“FairValueMeasurements”oftheseconsolidatedfinancialstatements.

6. Fair Value MeasurementsThe Company’s estimates of fair value for financial assets and liabilities are based on the framework established in the fair value accounting guidance

included in ASC Topic 820, “Fair Value Measurements and Disclosures.” The framework prioritizes the inputs, which refer broadly to assumptions marketparticipantswoulduseinpricinganassetorliability,intothreelevels.

TheCompanyconsiderspricesforactivelytradedsecuritiestobederivedbasedonquotedpricesinanactivemarketforidenticalassets,whichareLevel1inputsinthefairvaluehierarchy.Themajorityofthesesecuritiesarevaluedusingpricessuppliedbypricingservices.

TheCompanyconsiderspricesforothersecuritiesthatmaynotbeasactivelytradedwhicharepricedviapricingservices,vendorsandbroker-dealers, orwithreference tointerest rates andyieldcurves, to bederivedbasedoninputs that are observable for theasset, either directly or indirectly, whichare Level 2inputsinthefairvaluehierarchy.Themajorityofthesesecuritiesarealsovaluedusingpricessuppliedbypricingservices.

The Company considers securities, other financial instruments, privately-held investments and derivative insurance contracts subject to fair valuemeasurement whose valuation is derived by internal valuation models to be based largely on unobservable inputs, which are Level 3 inputs in the fair valuehierarchy.

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ThefollowingtablespresentthelevelwithinthefairvaluehierarchyatwhichtheCompany’sfinancialassetsandliabilitiesaremeasuredonarecurringbasisasatDecember31,2020andDecember31,2019: As at December 31, 2020 Level 1 Level 2 Level 3 Total ($ in millions)Available for sale financial assets, at fair value

U.S.government $ 1,101.2 $ — $ — $ 1,101.2U.S.agency — 34.3 — 34.3Municipal — 67.1 — 67.1Corporate 184.2 88.9 — 273.1Non-U.S.government-backedcorporate — 63.4 — 63.4Non-U.S.government — 7.4 — 7.4Asset-backed — 973.1 — 973.1Non-agencycommercialmortgage-backed — 2.3 — 2.3Agencymortgage-backed — 1,826.2 — 1,826.2

Totalfixedincomesecuritiesavailableforsale,atfairvalue 1,285.4 3,062.7 — 4,348.1Short-terminvestmentsavailableforsale,atfairvalue 81.0 6.8 — 87.8

Held for trading financial assets, at fair valueU.S.government 120.5 — — 120.5Municipal — 3.5 — 3.5Corporate — 103.5 — 103.5Highyieldloans — 9.8 — 9.8Non-U.S.government 41.2 0.4 — 41.6Asset-backed — 539.1 — 539.1Agencymortgage-backed — 37.6 — 37.6Totalfixedincomesecuritiestrading,atfairvalue 161.7 693.9 — 855.6Short-terminvestmentstrading,atfairvalue 35.4 — — 35.4Privately-heldinvestmentstrading,atfairvalue — — 299.3 299.3Catastrophebondstrading,atfairvalue — 18.8 — 18.8

Otherinvestments — — — 109.4

Other financial assets and liabilities, at fair valueDerivativesatfairvalue—foreignexchangecontracts — 26.8 — 26.8Liabilitiesunderderivativecontracts—foreignexchangecontracts — (13.6) — (13.6)Total 1,563.5 3,795.4 299.3 5,767.6

______________Otherinvestmentsrepresentsourinvestmentinarealestatefundandismeasuredatfairvalueusingthenetassetvaluepersharepracticalexpedient.Asaresultthishasnotbeenclassifiedinthefairvaluehierarchy.Thefairvalueamountspresentedinthetableaboveareintendedtopermitreconciliationofthefairvaluehierarchytotheamountspresentedintheconsolidatedbalancesheets.TheinvestmentintherealestatefundissubjecttorestrictionsasdetailedinNote20(a),“CommitmentsandContingencies.”

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At December 31, 2019 Level 1 Level 2 Level 3 Total ($ in millions)Available for sale financial assets, at fair value

U.S.government $ 1,413.1 $ — $ — $ 1,413.1U.S.agency — 39.6 — 39.6Municipal — 50.7 — 50.7Corporate — 1,959.8 — 1,959.8Non-U.S.government-backedcorporate — 86.5 — 86.5Non-U.S.government 199.8 129.0 — 328.8Asset-backed — 0.2 — 0.2Non-agencycommercialmortgage-backed — 6.5 — 6.5Agencymortgage-backed — 1,073.0 — 1,073.0

Totalfixedincomesecuritiesavailableforsale,atfairvalue 1,612.9 3,345.3 — 4,958.2Short-terminvestmentsavailableforsale,atfairvalue 108.1 9.5 — 117.6

Held for trading financial assets, at fair valueU.S.government 185.0 — — 185.0Municipal — 3.2 — 3.2Corporate — 243.2 — 243.2Non-U.S.government 48.3 102.9 — 151.2Asset-backed — 492.4 — 492.4Agencymortgage-backed — 53.8 — 53.8

Totalfixedincomesecuritiestrading,atfairvalue 233.3 895.5 — 1,128.8Short-terminvestmentstrading,atfairvalue 79.2 — — 79.2Privately-heldinvestments — — 279.7 279.7Catastrophebondstrading,atfairvalue — 28.6 — 28.6

Otherinvestments — — — 111.4

Other financial assets and liabilities, at fair valueDerivativesatfairvalue—foreignexchangecontracts — 12.9 — 12.9Derivativesatfairvalue—interestrateswaps — (78.3) — (78.3)Liabilitiesunderderivativecontracts—foreignexchangecontracts — (8.9) — (8.9)Loannotesissuedbyvariableinterestentities,atfairvalue(includedwithinaccruedexpensesandotherpayables) — — — —

Total $ 2,033.5 $ 4,204.6 $ 279.7 $ 6,629.2

______________Otherinvestmentsrepresentsourinvestmentinarealestatefundandismeasuredatfairvalueusingthenetassetvaluepersharepracticalexpedient.Asaresultthishasnotbeenclassifiedinthefairvaluehierarchy.Thefairvalueamountspresentedinthetableaboveareintendedtopermitreconciliationofthefairvaluehierarchytotheamountspresentedintheconsolidatedbalancesheets.TheinvestmentintherealestatefundissubjecttorestrictionsasdetailedinNote20(a),“CommitmentsandContingencies.”

Transfersofassetsintooroutofaparticularlevelarerecordedattheirfairvaluesasoftheendofeachreportingperiodconsistentwiththedateofthedeterminationoffairvalue.DuringthetwelvemonthsendedDecember31,2020,$8.3millionwastransferredfromLevel2toLevel3duetoachangeinpricingmethodology.(December31,2019,notransfersweremadebetweenLevel1,Level2andLevel3)

AsatDecember31,2020,therewereprivately-heldinvestmentsworth$299.3million(December31,2019—$279.7million)classifiedasLevel3.AsaresultofloanssoldbyAspenandloansrepaidtoAspenbyborrowers,anetsettlementof$64.3millionoccurredduringtheyear.

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Asat December 31, 2019, theCompanysettled$23.9millionworthof Level 3assets andtheCompany’sLevel 3liabilities consistedsolelyof theLoanNotes issued by Silverton. The Companysettled $3.1 million Level 3 liabilities in respect to the Loan Notes issued by Silverton for the twelve months endedDecember31,2019.

ThefollowingtablepresentsareconciliationofthebeginningandendingbalancesforallassetsandliabilitiesmeasuredatfairvalueonarecurringbasisusingLevel3inputsforthetwelvemonthsendedDecember31,2020andDecember31,2019:

Twelve Months Ended December 31, 2020

Balance atbeginning of

yearPurchases and

issuancesTransfersin/(out)

Settlements andsales

Increase/(decrease)in fair valueincluding netincome

Balance atend of year

Change inunrealized

investment gains(losses) relating toassets held at end

of yearAssetsPrivately-heldinvestments—tradingCommercialmortgageloans $ 156.4 $ 79.7 $ — $ (59.4) $ (13.1) $ 163.6 $ 0.1Middlemarketloans 111.7 0.9 8.3 (4.8) (4.0) 112.1 (5.3)Asset-backedsecurities 8.7 10.0 — — (0.1) 18.6 —Equitysecurities 2.7 2.4 — (0.1) — 5.0 —Total Level 3 assets $ 279.5 $ 93.0 $ 8.3 $ (64.3) $ (17.2) $ 299.3 $ (5.2)

LiabilitiesLoannotesissuedbySilverton $ — $ — $ — $ — $ — $ — $ —

Total Level 3 liabilities $ — $ — $ — $ — $ — $ — $ —

Twelve Months Ended December 31, 2019AssetsPrivately-heldinvestments—tradingCommercialmortgageloans $ — $ 174.7 $ — $ (20.1) $ 1.7 $ 156.4 $ 0.3Middlemarketloans — 115.5 — (3.8) 0.1 111.7 —Asset-backedsecurities — 8.7 — — — 8.7 —Equitysecurities — 2.7 — — — 2.7 —Total Level 3 assets $ — $ 301.5 $ — $ (23.9) $ 1.8 $ 279.5 $ 0.3

LiabilitiesLoannotesissuedbySilverton $ 4.6 $ — $ — $ (7.7) $ 3.1 $ — $ —

Total Level 3 liabilities $ 4.6 $ — $ — $ (7.7) $ 3.1 $ — $ —

Valuation of Fixed Income Securities.TheCompany’sfixedincomesecuritiesareclassifiedaseitheravailableforsaleortradingandarecarriedatfairvalue.AsatDecember31,2020andDecember31,2019,theCompany’sfixedincomesecuritieswerevaluedbypricingservicesorbroker-dealersusingstandardmarketconventions. The market conventions utilize market quotations, market transactions in comparable instruments and various relationships between instrumentsincluding,butnotlimitedto,yieldtomaturity,dollarpricesandspreadpricesindeterminingvalue.

Independent Pricing Services. Theunderlyingmethodologyusedtodeterminethefair valueof securities in theCompany’s available for sale andtradingportfoliosisbythepricingservices.Pricingserviceswillgatherobservablepricinginputsfrommultipleexternalsources,includingbuyandsell-sidecontactsandbroker-dealers,inordertodeveloptheirinternalprices.

Pricingservicesprovidepricingforlesscomplex,liquidsecuritiesbasedonmarketquotationsinactivemarkets.Pricingservicessupplypricesforabroadrangeofsecuritiesincludingthoseforactivelytradedsecurities,suchasTreasuryandother

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Governmentsecurities,inadditiontothosethattradelessfrequentlyorwherevaluationincludesreferencetocreditspreads,paydownandpre-payfeaturesandotherobservableinputs.ThesesecuritiesincludeGovernmentagency,municipals,corporateandasset-backedsecurities.

For securities that maytrade less frequently or do not trade on a listed exchange, these pricing services mayuse matrix pricing consisting of observablemarket inputs to estimate the fair value of a security. These observable market inputs include: reported trades, benchmark yields, broker-dealer quotes, issuerspreads, two-sided markets, benchmark securities, bids, offers, reference data, and industry and economic factors. Additionally, pricing services may use avaluationmodelsuchasanoptionadjustedspreadmodelcommonlyusedforestimatingfairvaluesofmortgage-backedandasset-backedsecurities.TheCompanydoesnotderivedollarpricesusinganindexasapricinginputforanyindividualsecurity.

Broker-Dealers.The Company obtains quotes from broker-dealers who are active in the corresponding markets when prices are unavailable fromindependentpricingservicesorindexproviders. Generally, broker-dealersvaluesecuritiesthroughtheirtradingdesksbasedonobservablemarketinputs. Theirpricingmethodologiesincludemappingsecuritiesbasedontradedata,bidsoroffers,observedspreadsandperformanceofnewlyissuedsecurities.Theymayalsoestablishpricingthroughobservingsecondarytradingofsimilarsecurities.Quotesfrombroker-dealersarenon-binding.

The Companyobtains prices for all of its fixed incomeinvestment securities via its third-party accounting service provider, and in the majority of casesreceivinganumberofquotessoastoobtainthemostcomprehensiveinformationavailabletodetermineasecurity’sfairvalue.AsinglevaluationisappliedtoeachsecuritybasedonthevendorhierarchymaintainedbytheCompany’sthird-partyaccountingserviceprovider.

AsatDecember31,2020,theCompanyobtainedanaverageof2.6quotesperfixedincomeinvestmentcomparedto2.4quotesatDecember31,2019.TheCompany,inconjunctionwithitsthird-partyaccountingserviceprovider,obtainsanunderstandingofthemethods,modelsandinputsusedbythethird-

partypricingserviceandindexproviderstoassesstheongoingappropriatenessofvendors’prices.TheCompanyanditsthird-partyaccountingserviceprovideralsohavecontrolsinplacetovalidatethatamountsprovidedrepresentfairvalues.Processestovalidateandreviewpricinginclude,butarenotlimitedto:

• quantitativeanalysis(e.g.,comparingthequarterlyreturnforeachmanagedportfoliotoitstargetbenchmark,withsignificantdifferencesidentifiedandinvestigated);

• comparison of market values obtained from pricing services and broker-dealers against alternative price sources for each security where furtherinvestigationiscompletedwhensignificantdifferencesexistforpricingofindividualsecuritiesbetweenpricingsources;

• initialandongoingevaluationofmethodologiesusedbyoutsidepartiestocalculatefairvalue;and• comparisonofthefairvalueestimatestotheCompany’sknowledgeofthecurrentmarket.Pricesobtainedfrompricingservicesandbroker-dealers arenotadjustedbyus;however, pricesprovidedbyapricingservice, orbroker-dealer incertain

instancesmaybechallengedbasedonmarketorinformationavailablefrominternalsources,includingthoseavailabletotheCompany’sthird-partyinvestmentaccounting service provider. Subsequent to any challenge, revisions made by the pricing service or broker-dealer to the quotes are supplied to the Company’sinvestmentaccountingserviceprovider.

ManagementreviewsthevendorhierarchymaintainedbytheCompany’sthird-partyaccountingserviceproviderinordertodeterminewhichpricesourceprovidesthemostappropriatefairvalue(i.e.,apriceobtainedfromapricingservicewithmoreseniorityinthehierarchywillbeusedoveralesssenioroneinallcases).ThehierarchylevelassignedtoeachsecurityintheCompany’savailableforsaleandtradingportfoliosisbaseduponitsassessmentofthetransparencyandreliabilityoftheinputsusedinthevaluationasofthemeasurementdate.Thehierarchyofpricingservicesisdeterminedusingvariousqualitativeandquantitativepoints arising fromreviews of the vendors conducted by the Company’s third-party accounting service provider. Vendor reviews include annual due diligencemeetingswithindexprovidersandpricingservicesvendorscoveringvaluationmethodology,operationalwalkthroughsandlegalandcomplianceupdates.

Fixed Income Securities.Fixedincomesecuritiesaretradedontheover-the-counter(“OTC”)marketbasedonpricesprovidedbyoneormoremarketmakersineachsecurity.SecuritiessuchasU.S.Government,U.S.Agency,ForeignGovernmentandinvestmentgradecorporatebondshavemultiplemarketmakersinadditiontoreadilyobservablemarketvalueindicatorssuchasexpectedcredit spread,exceptforTreasurysecurities, overtheyieldcurve.TheCompanyusesavarietyofpricingsourcestovaluefixedincomesecuritiesincludingthosesecuritiesthathavepaydown/prepayfeaturessuchasmortgage-backedsecuritiesandasset-backedsecuritiesinordertoensurefairandaccuratepricing.ThefairvalueestimatesfortheinvestmentgradesecuritiesintheCompany’sportfoliodonotusesignificantunobservableinputsormodelingtechniques.

U.S. Government and Agency Securities.U.S.governmentandagencysecuritiesconsistprimarilyofbondsissuedbytheU.S.TreasuryandcorporatedebtissuedbyagenciessuchastheFederal National MortgageAssociation(“FNMA”), theFederal HomeLoanMortgageCorporation(“FHLMC”)andtheFederalHomeLoanBank.AsthefairvaluesofU.S.Treasury

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securities arebasedonunadjustedmarket pricesinactivemarkets, theyareclassifiedwithinLevel1. Thefair valuesofU.S.governmentagencysecurities arepricedusingthespreadabovetherisk-freeyieldcurve.Astheyieldsfortherisk-freeyieldcurveandthespreadsforthesesecuritiesareobservablemarketinputs,thefairvaluesofU.S.governmentagencysecuritiesareclassifiedwithinLevel2.

Municipal Securities.TheCompany’smunicipalportfolioconsistofbondsissuedbyU.S.domiciledstateandmunicipalityentities.Thefairvalueofthesesecuritiesisdeterminedusingspreadsobtainedfrombroker-dealers, tradepricesandthenewissuemarketwhichareLevel2inputsinthefairvaluehierarchy.Consequently,thesesecuritiesareclassifiedwithinLevel2.

Non-U.S. Government.Theissuersforsecuritiesinthiscategoryarenon-U.S.governmentsandtheiragentsincluding,butnotlimitedto,theU.K.,Australia,Canada,FranceandGermany.Thefairvaluesofcertainnon-U.S.governmentbonds,primarilysourcedfrominternationalindices,arebasedonunadjustedmarketpricesinactivemarketsandarethereforeclassifiedwithinLevel1.Theremainingnon-U.S.governmentbondsareclassifiedwithinlevel2astheyarenotactivelytraded.Thefairvaluesofthenon-U.S.agencysecurities,againprimarilysourcedfrominternationalindices,arepricedusingthespreadabovetherisk-freeyieldcurve.Astheyieldsfortherisk-freeyieldcurveandthespreadsforthesesecuritiesareobservablemarketinputs,thefairvaluesofnon-U.S.agencysecuritiesareclassifiedwithinLevel2. Inaddition, foreigngovernmentsecurities includeaportionoftheEmergingMarket Debt(“EMD”)portfoliowhichis alsoclassifiedwithinLevel2.

Corporate. Corporatesecuritiesconsistprimarilyofshort-term,medium-termandlong-termdebtissuedbyU.S.andforeigncorporationscoveringavarietyof industries and are generally priced by index providers and pricing vendors. Some issuers may participate in government programs which guarantee timelypaymentofprincipalandinterestintheeventofadefault.Thefairvaluesofthesesecuritiesaregenerallydeterminedusingthespreadabovetherisk-freeyieldcurve.Inputsusedintheevaluationofthesesecuritiesincludecreditdata,interestratedata,marketobservationsandsectornews,broker-dealerquotesandtradevolumes.Inaddition,corporatesecuritiesincludeaportionoftheEMDportfolio.TheCompanyclassifiesthesesecuritiesacrossLevel1and2,withmajorityofthembeinginLevel1.

Mortgage-backed Securities.Residential and commercial mortgage-backed securities consist of bonds issued by the Government National MortgageAssociation, the FNMAandthe FHLMCas well as private non-agencyissuers. Thefair values of these securities are determined throughthe use of a pricingmodel(includingOptionAdjustedSpread)whichusesprepaymentspeedsandspreadstodeterminetheappropriateaveragelifeofthemortgage-backedsecurity.Thesespreadsaregenerallyobtainedfrombroker-dealers,tradepricesandthenewissuemarket.Asthesignificantinputsusedtopricemortgage-backedsecuritiesareobservablemarketinputs,thesesecuritiesareclassifiedwithinLevel2.

Asset-backed Securities.Asset-backedsecuritiesaresecuritiesbackedbynotesorreceivablesagainstassetsotherthanrealestate.TheunderlyingcollateralfortheCompany’sasset-backedsecuritiesconsistsmainlyofstudentloans,automobileloansandcreditcardreceivables.Thesesecuritiesareprimarilypricedbyindexprovidersandpricingvendors.Inputstothevaluationprocessincludebroker-dealerquotesandotheravailabletradeinformation,prepaymentspeeds,interestratedataandcreditspreads.TheCompanyclassifiesthesesecuritieswithinLevel2.

Short-term Investments.Short-terminvestmentsconsistofhighlyliquiddebtsecuritieswithamaturitygreaterthanthreemonthsbutlessthanoneyearfromthedateofpurchase.Short-terminvestmentsareclassifiedaseithertradingoravailableforsaleaccordingtothefactsandcircumstancesoftheinvestmentheld.Short-terminvestmentsarevaluedinamannersimilartotheCompany’sfixedmaturityinvestmentsandareclassifiedwithinLevels1and2.

Privately-Held Investments. Privately-held investments are initially valued at cost or transaction value which approximates fair value. In subsequentmeasurementperiods,thefairvaluesofthesesecuritiesaredeterminedusinginternallydevelopeddiscountedcashflowmodels.Thesemodelsincludeinputsthatarespecifictoeachinvestment.Theinputsusedinthefairvaluemeasurementsincludedividendorinterestratesandappropriatediscountrates.Theselectionofanappropriatediscountrateisjudgmentalandisthemostsignificantunobservableinputusedinthevaluationofthesesecurities.Asignificantincrease(decrease)inthisinputinisolationcouldresultinsignificantlylower(higher)fairvaluemeasurementforprivately-heldinvestments.InordertoassessthereasonablenessoftheinputstheCompanyusesinthediscountedcashflowmodels,theCompanymaintainsanunderstandingofcurrentmarketconditions,issuerspecificinformationthatmayimpactfuturecashflowsaswell ascollaborationwithindependentvendorsformostsecurities toassessthereasonablenessofthediscountratebeingused.

ThefollowingtablesummarizesthequantitativeinputsandassumptionsusedforfinancialassetsandliabilitiescategorizedasLevel3underthefairvaluehierarchyasatDecember31,2020:

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At December 31, 2020Fair Value

Level 3 Valuation Techniques Unobservable (U) inputs RangesWeightedAverage

($ in millions)Privately-held investments — TradingCommercialmortgageloans $ 150.8 Discountedcashflow Discountrate 6.0% — 9.0% 7.3%

Commercialmortgageloans 12.1 TransactionValue n/a n/a n/a n/aCommercialmortgageloans 0.7 LiquidationMethod n/a n/a n/a n/aMiddlemarketloans 106.5 Discountedcashflow Discountrate 6.3% — 16.5% 8.7%Middlemarketloans 5.6 RecoveryApproach n/a n/a n/a n/a

Asset-backedsecurities 18.6 Discountedcashflow Discountrate 5.7% — 6.9% 6.2%Equitysecurities 4.3 Discountedcashflow Discountrate 9.3% n/a 9.3%Equitysecurities 0.7 TransactionValue n/a n/a n/a n/a

$ 299.3

Catastrophe Bonds. Catastrophe bonds are variable rate fixed incomeinstruments with redemption values adjusted based on the occurrence of a coveredevent,usuallywindstormsandearthquakes.Catastrophebondsareclassifiedastradingandcarriedatfairvalue.Catastrophebondsarepricedusinganaverageofmultiplebroker-dealerquotesandassuch,areconsideredLevel2.

Foreign Exchange Contracts.The foreign exchange contracts which the Company uses to mitigate currency risk are characterized as OTC due to theircustomized nature and the fact that they do not trade on a major exchange. These instruments trade in a very deep liquid market, providing substantial pricetransparencyandaccordinglyareclassifiedasLevel2.

Interest Rate Swaps.TheinterestrateswapswhichtheCompanyusedtomitigateinterestriskarecharacterizedasOTCandarevaluedbythecounterpartyusingquantitativemodelswithmultiplemarketinputs.Themarketinputs,suchasinterestratesandyieldcurves,areobservableandthevaluationcanbecomparedforreasonablenesswiththird-partypricingservices.Consequently,theseinstrumentsareclassifiedasLevel2.During2020,weunwoundtheremaining$1,800.0millionofourinterestrateswaps.

Other investments. TheCompany’sotherinvestmentsrepresentourinvestmentinarealestatefund.Adjustmentstothefairvaluearemadebasedonthenetasset value of the investment. The net valuation criteria established by the manager of such investments are established in accordance with the governingdocumentsandtheassetmanager’svaluationguidelines,whichconsideratwopartapproach:thediscountedcashflowsapproachandtheperformancemultipleapproach,whichusesamultiple/capitalizationratederivedfrommarketmetricsfromcomparablecompaniesorassetstoproduceoperatingperformancemetrics.Alternativevaluationmethodologiesmaybeemployedforinvestmentswithunusualcharacteristics.

7. ReinsuranceTheCompanypurchasesretrocessionandreinsurancetolimitanddiversifytheCompany’sriskexposureandtoincreaseitsowninsuranceandreinsurance

underwriting capacity. These agreements provide for recovery of a portion of losses and loss adjustment expenses from reinsurers. As is the case with mostreinsurance contracts, the Company remains liable to the extent that reinsurers do not meet their obligations under these agreements. In line with its riskmanagementobjectives,theCompanyevaluatesthefinancialconditionofitsreinsurersandmonitorsconcentrationsofcreditrisk.

Balancespertainingtoreinsurancetransactionsarereported“gross”ontheconsolidatedbalancesheet,meaningthatreinsurancerecoverableonunpaidlossesandcededunearnedpremiumsare not deductedfrominsurance reserves but are recordedas assets. For more information onreinsurance recoverables, refer toNote21,“ConcentrationsofCreditRisk—Reinsurancerecoverables”andNote10,“ReservesforLossesandLossAdjustmentExpenses”oftheseconsolidatedfinancialstatements.

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The effect of assumed and ceded reinsurance on premiums written, premiums earned and insurance losses and loss adjustment expenses for the twelvemonthsendedDecember31,2020,2019and2018wasasfollows: Twelve Months Ended December 31, 2020 2019 2018 ($ in millions)Premiums written:

Direct $ 2,042.8 $ 1,956.9 $ 1,951.2Assumed 1,660.8 1,485.5 1,495.7Ceded (1,120.7) (1,014.5) (1,364.9)Netpremiumswritten $ 2,582.9 $ 2,427.9 $ 2,082.0

Premiums earned:

Direct $ 2,027.1 $ 1,927.5 $ 1,940.5Assumed 1,616.4 1,494.9 1,593.9Ceded (1,110.9) (1,129.1) (1,319.7)Netpremiumsearned $ 2,532.6 $ 2,293.3 $ 2,214.7

Insurance losses and loss adjustment expenses:

Direct $ 1,479.6 $ 1,415.5 $ 1,458.9Assumed 1,134.5 1,147.9 1,196.1Ceded (773.3) (883.7) (1,082.0)Net insurance losses and loss adjustment expenses $ 1,840.8 $ 1,679.7 $ 1,573.0

OnMarch2,2020,theCompanyenteredintoanadversedevelopmentcoverreinsuranceagreementwithasubsidiaryofEnstarGroupLimited(“Enstar”),pursuanttowhichEnstar’ssubsidiarywillreinsurelossesincurredonorpriortoDecember31,2019.Enstar’ssubsidiarywillprovide$770.0millionofcoverinexcess of $3.805billionretention upto anaggregate of $4.575billion, andanadditional $250.0million of cover in excess above$4.815billion,upto $5.065billion.AsaresultoftheADC,wehavesignificantlyreducedourexposuretoclaimsfromrisksunderwrittenonorpriortoDecember31,2019,andweexpecttheADCtosignificantlyreducevolatilityfromourhistoricalbusinessgoingforward.

OnJune16,2016,theFASBissuedASU2016-13,“FinancialInstruments—CreditLosses(Topic326)”whichintroducedanewimpairmentmodel,knownasthecurrentexpectedlossmodel(“CECL”),whichisbasedonexpectedlossesratherthanincurredlosses.Underthenewcreditlossmodel,theCompanywouldrecognizeanallowanceforitsestimateofexpectedcredit lossesandthiswouldapplytoreinsurancereceivables. ForamoredetaileddescriptionofaccountingpoliciesforCECLandOTTI,refertoNote2(c),“BasisofPreparationandSignificantAccountingPolicies”oftheseconsolidatedfinancialstatements.

CECL. Following the adoption of this ASU with effect from January 1, 2020, the Company recognized a reduction in the Company’s reinsurancerecoverablesby$3.7millionasaresultofrecognizingCECLthroughopeningretainedearningsforperiods2019andprior.

ForthetwelvemonthsendedDecember31,2020therewasanincreaseintheCECLallowanceonreinsurancerecoverablesof$0.1million.TheCompanyispotentiallyexposedtoconcentrationsofcreditriskinrespectofamountsrecoverablefromreinsurers,refertoNote21,“Concentrationsof

CreditRisk—Reinsurancerecoverables”formoredetail.

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8. Derivative ContractsThefollowingtablesummarizesinformationonthelocationandamountsofderivativefairvaluesontheconsolidatedbalancesheetasatDecember31,2020

and2019: As at December 31, 2020 As at December 31, 2019 Derivatives Not Designated as HedgingInstruments Under ASC 815 Balance Sheet Location

Notional Amount

Fair Value

Notional Amount

Fair Value

($ in millions) ($ in millions) ForeignExchangeContracts DerivativesatFairValue $ 803.1 $ 21.5 $ 687.3 $ 8.1ForeignExchangeContracts LiabilitiesunderDerivativeContracts $ 599.2 $ (13.6) $ 1,009.0 $ (8.9)InterestRateSwaps LiabilitiesunderDerivativeContracts $ — $ — $ 1,800.0 $ (78.3)

______________Netof$3.4millionofcashcollateral(December31,2019—$2.9million).Initialandvariationmarginof$Nilhasbeenposted(December31,2019—$111.1million).

As at December 31, 2020 As at December 31, 2019 Derivatives Designated as HedgingInstruments Under ASC 815 Balance Sheet Location

Notional Amount

Fair Value

Notional Amount

Fair Value

($ in millions) ($ in millions) ForeignExchangeContracts DerivativesatFairValue $ 90.6 $ 5.3 $ 85.5 $ 4.8

The following table provides the unrealized and realized gains/(losses) recorded in the statements of operations and other comprehensive income forderivativesthatarenotdesignatedordesignatedashedginginstrumentsunderASC815—“Derivatives and Hedging”forthetwelvemonthsendedDecember31,2020and2019:

Amount of (Loss)/Gain Recognized on DerivativesFor the Twelve Months Ended

Location of Gain/(Loss) Recognized on Derivatives December 31, 2020 December 31, 2019

Derivatives not designated as hedges ($ in millions)ForeignExchangeContracts ChangeinFairValueofDerivatives 16.0 (14.0)InterestRateSwaps ChangeinFairValueofDerivatives (81.1) (130.2)

Derivatives designated as hedgesForeignExchangeContracts General,administrativeandcorporateexpenses (3.2) 0.9

ForeignExchangeContractsNetchangefromcurrentperiodhedgedtransactions 0.3 4.8

Foreign Exchange Contracts.TheCompanyusesforeignexchangecontractstomanageforeigncurrencyriskassociatedwithouroperatingexpensesbutalsoforeign exchange risk associated with net assets or liabilities in currencies other than the U.S. dollar. A foreign exchange contract involves an obligation topurchaseorsellaspecifiedcurrencyatafuturedateatapricesetatthetimeofthecontract.ForeignexchangecontractswillnoteliminatefluctuationsinthevalueoftheCompany’sassetsandliabilitiesdenominatedinforeigncurrenciesbutratherallowittoestablisharateofexchangeforafuturepointintime.

As at December 31, 2020, the Company held foreign exchange contracts that were not designated as hedges under ASC815 with an aggregate nominalamountof$1,402.3million(2019—$1,696.3million).Theforeignexchangecontractsarerecordedasderivativesatfairvalueinthebalancesheetwithchangesrecordedasachangeinfairvalueofderivativesinthestatementofoperations.ForthetwelvemonthsendedDecember31,2020,theimpactofforeignexchangecontractsonnetincomewasagainof$16.0million(December31,2019—lossof$14.0million).

AsatDecember31,2020,theCompanyheldforeignexchangecontractsthatweredesignatedashedgesunderASC815withanaggregatenominalamountof$90.6million(2019—$85.5million).Theforeignexchangecontractsarerecordedasderivativesatfairvalueinthebalancesheetwiththeeffectiveportionrecordedinothercomprehensiveincomeandtheineffectiveportionrecordedasachangeinfairvalueofderivativesinthestatementofoperations.Thecontractsare considered to be effective and therefore the movement in other comprehensive income representing the effective portion for the twelve months endedDecember31,2020wasagainof$0.3million(December31,2019—gainof$4.8million).

Astheforeignexchangecontractssettle,therealizedgainorlossisreclassifiedfromothercomprehensiveincomeintogeneral,administrationandcorporateexpensesofthestatementofoperationsandothercomprehensiveincome.Forthetwelve

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months ended December 31, 2020, the amount recognized within general, administration and corporate expenses for settled foreign exchange contracts was arealizedlossof$3.2million(December31,2019—gainof$0.9million).

Interest Rate Swaps.In the first quarter of 2019, the Company entered into fixed for floating interest rate swaps with a total notional amou nt of$3,138.0 million due to mature between January 18, 2021 and January 18, 2034. The interest rate swaps were used in the ordinary course of the Company’sinvestmentsactivitiestopartiallymitigateanynegativeimpactofrisesininterestratesonthemarketvalueoftheCompany’sfixedincomeportfolio.During2020,we unwound the remaining $1,800.0 million of our interest rate swaps. For the twelve months ended December 31, 2020, there was a loss of $81.1 million(December31,2019—$130.2million).

AsatDecember31,2020,nomarginwaspostedtoaFuturesCommissionMerchantaswewounduptheinterestrateswaps.AsatDecember31,2020,nonon-cash collateral was transferred to the Company by its counterparties (December 31, 2019 —$Nil). Transfers of margin are recorded on the consolidatedbalance sheet within Derivatives at Fair Value, while transfers in respect of non-cash collateral are disclosed but not recorded. As at December 31, 2020, noamountwasrecordedintheconsolidatedbalancesheetforthepledgedassets.

9. Deferred Policy Acquisition CostsThefollowingtablerepresentsareconciliationofbeginningandendingdeferredpolicyacquisitioncostsforthetwelvemonthsendedDecember31,2020

and2019:Twelve Months Ended

December 31, 2020Twelve Months Ended

December 31, 2019($ in millions)

Balanceatthebeginningoftheperiod $ 291.1 $ 248.5Acquisitioncostsdeferred 481.2 455.3Amortizationofdeferredpolicyacquisitioncosts (465.7) (412.7)

Balanceattheendoftheperiod $ 306.6 $ 291.1

10. Reserves for Losses and Loss Adjustment ExpensesThefollowingtablerepresentsareconciliationofbeginningandendingconsolidatedlossandLAEreservesforthetwelvemonthsendedDecember31,2020,

2019and2018:

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As at December 31,2020 2019 2018

($ in millions)ProvisionforlossesandLAEatthestartoftheyear $ 6,951.8 $ 7,074.2 $ 6,749.5Lessreinsurancerecoverable (2,319.8) (2,077.6) (1,515.2)NetlossandLAEatthestartoftheyear 4,632.0 4,996.6 5,234.3

NetlossandLAEexpenses(disposed) (818.5) — —MovementinnetprovisionforlossesandLAEforclaimsincurred:

Currentyear 1,841.7 1,620.2 1,684.1Prioryears (0.9) 59.5 (111.1)Totalincurred 1,840.8 1,679.7 1,573.0

LossesandLAEpaymentsforclaimsincurred:Currentyear (404.9) (428.5) (285.7)Prioryears (1,359.7) (1,694.1) (1,441.0)Totalpaid (1,764.6) (2,122.6) (1,726.7)

Foreignexchangelosses/(gains) 80.4 78.3 (84.0)

NetlossesandLAEreservesattheendoftheyear 3,970.1 4,632.0 4,996.6Plusreinsurancerecoverableonunpaidlossesattheendoftheyear 3,195.2 2,319.8 2,077.6ProvisionforlossesandLAEattheendoftheyear $ 7,165.3 $ 6,951.8 $ 7,074.2

______________NetlossandLAEexpensesdisposedincludestheadversedevelopmentcoverreinsuranceagreementproviding$770.0millionofcoverandthelossportfoliotransfertransactionsforoursuretyinsurancebookof$42.0millionandourU.S.accidentandhealthbookof$6.5million.ForthetwelvemonthsendedDecember31,2020,therewasareductionof$0.9millionintheCompany’sestimateoftheultimateclaimstobepaidinrespect

ofprioraccidentyearscomparedtoanincreaseof$59.5millionforthetwelvemonthsendedDecember31,2019.

Overall,prioryearreservereleasestotaled$0.9millionin2020,comparedwithnetunfavorablereservedevelopmentof$59.5millionin2019.Reservereleasesin the reinsurance segment in 2020were $36.1 million compared to $54.9 million in 2019andcameprimarily fromcasualty reinsurance, property catastrophereinsuranceandspecialtyreinsurance,partiallyoffsetbystrengtheningonotherpropertyreinsurancelines.Netunfavorablereservedevelopmentintheinsurancesegmentin2020was$35.2millioncomparedtonetunfavorablereservedevelopmentof$114.4millionin2019andcameprimarilyfrompropertyandcasualtyinsurancelines.

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Thefollowingtablesshowananalysisofincurredclaimsandallocatedlossadjustmentexpenses,netofreinsuranceandcumulativepaidclaimsandallocatedclaimadjustmentexpenses,netofreinsuranceasatDecember31,2020,2019,2018,20172016,2015,2014,2013and2012.ThelossdevelopmenttrianglesarederivedfromallbusinesswrittenbytheCompanyasalthoughalimitednumberofcontractsarewrittenwhichhavedurationsofgreaterthanoneyearthecontractsdonotmeetthedefinitionofalongdurationcontract.AllamountsincludedinthefollowingtablesrelatedtotransactionsdenominatedinaforeigncurrencyhavebeentranslatedintoU.S.DollarsusingtheexchangeratesineffectatDecember31,2020.

Property Insurance LinesIncurred Claims, IBNR and Loss Adjustment Expenses, Net of Reinsurance As at December 31, 2020

Total of IBNR PlusExpected

Development onReported Claims

Cumulative Numberof Reported Claims

For the Years Ended December 31,

Accident Year

Unaudited Prior Years

2012 2013 2014 2015 2016 2017 2018 2019 2020

$ (in millions)2012 171.1 168.9 167.7 166.7 161.1 155.2 154.1 154.2 154.8 — 6,0802013 131.2 118.2 117.9 113.6 114.6 112.6 112.9 113.1 0.7 5,7422014 166.5 158.2 135.0 135.6 134.9 133.3 132.7 0.6 9,9692015 242.7 208.1 202.5 204.9 205.3 202.1 2.9 11,5832016 240.5 251.2 246.1 247.4 248.9 3.5 10,7652017 298.4 261.2 254.4 255.7 (6.5) 9,6392018 207.2 210.0 193.5 (13.3) 8,1062019 129.2 132.7 11.7 6,5922020 207.5 64.7 5,706

Total $ 1,641.0

Property Insurance LinesCumulative Paid Claims and Allocated Loss Adjustment Expenses, Net of Reinsurance

For the Years Ended December 31, Unaudited Prior Years

Accident Year 2012 2013 2014 2015 2016 2017 2018 2019 2020 ($ in millions)2012 41.6 129.8 139.6 153.9 158.0 155.4 154.8 154.7 154.72013 39.4 76.7 90.0 102.1 106.7 109.4 111.2 111.52014 40.6 87.1 114.7 124.5 128.6 130.1 131.32015 57.6 144.6 172.7 181.9 198.6 197.02016 67.5 170.1 202.9 225.3 234.22017 97.4 190.5 224.0 244.92018 63.1 164.5 186.62019 49.8 93.02020 62.1

Total $ 1,415.3

Alloutstandingliabilitiesfor2012andsubsequentyears,netofreinsurance $ 225.7Alloutstandingliabilitiesbefore2012,netofreinsurance(unaudited) 1.1

Liabilitiesforclaimsandclaimadjustmentexpenses,netofreinsurance $ 226.8

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Casualty Insurance LinesIncurred Claims, IBNR and Loss Adjustment Expenses, Net of Reinsurance As at December 31, 2020

Total of IBNR PlusExpected

Development onReported Claims

Cumulative Numberof Reported Claims

For the Years Ended December 31,

Accident Year

Unaudited Prior Years

2012 2013 2014 2015 2016 2017 2018 2019 2020

$ (in millions)2012 78.8 63.7 70.8 62.0 69.9 67.5 69.4 71.4 67.6 1.9 3,0162013 134.6 117.9 116.3 121.9 104.8 106.1 106.2 100.5 3.6 3,3112014 147.0 129.2 141.1 131.5 138.7 142.8 131.1 5.9 3,8072015 206.2 226.2 188.8 207.0 240.0 223.5 17.9 4,6822016 220.2 191.4 186.8 193.6 194.1 34.7 4,6972017 184.0 177.4 181.6 188.3 27.8 5,2972018 124.9 127.7 127.3 43.0 5,4402019 127.4 132.3 70.1 4,9582020 135.7 120.2 2,964

Total 1,300.4

Casualty Insurance LinesCumulative Paid Claims and Allocated Loss Adjustment Expenses, Net of Reinsurance

For the Years Ended December 31, Unaudited Prior Years

Accident Year 2012 2013 2014 2015 2016 2017 2018 2019 2020 ($ in millions)2012 1.4 6.8 14.4 30.1 41.5 49.9 50.8 55.5 60.22013 2.3 26.0 40.0 53.7 69.3 82.0 86.3 88.42014 2.8 13.6 33.2 60.7 74.5 99.1 112.22015 3.2 17.3 57.2 94.0 140.5 170.12016 4.3 23.2 41.0 84.3 111.92017 3.7 23.3 53.7 99.12018 3.3 28.3 44.52019 6.5 18.82020 —

Total $ 705.2

Alloutstandingliabilitiesfor2012andsubsequentyears,netofreinsurance $ 595.2Alloutstandingliabilitiesbefore2012,netofreinsurance(unaudited) 23.5

Liabilitiesforclaimsandclaimadjustmentexpenses,netofreinsurance $ 618.7

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Marine, Aviation and Energy Insurance LinesIncurred Claims, IBNR and Loss Adjustment Expenses, Net of Reinsurance As at December 31, 2020

Total of IBNR PlusExpected

Development onReported Claims

Cumulative Numberof Reported Claims

For the Years Ended December 31,Unaudited Prior Years

Accident Year 2012 2013 2014 2015 2016 2017 2018 2019 2020

$ (in millions)2012 270.4 307.7 327.2 348.0 333.6 329.6 318.0 312.7 303.1 0.6 3,8122013 321.8 334.7 343.3 326.7 333.7 347.2 346.0 340.7 — 4,1752014 310.5 315.0 299.8 311.4 306.9 313.8 301.6 — 4,0492015 298.4 301.8 284.1 287.9 311.5 313.5 — 4,0532016 262.7 232.2 231.7 231.8 218.5 — 4,4162017 211.7 201.7 208.1 201.5 7.8 6,0012018 172.4 209.5 202.6 13.7 5,1332019 147.3 148.4 27.5 3,4662020 111.5 56.8 2,321

Total 2,141.4

Marine, Aviation and Energy Insurance LinesCumulative Paid Claims and Allocated Loss Adjustment Expenses, Net of Reinsurance

For the Years Ended December 31, Unaudited Prior Years

Accident Year 2012 2013 2014 2015 2016 2017 2018 2019 2020 ($ in millions)2012 52.4 133.6 176.2 212.5 241.4 252.3 275.2 276.1 278.22013 41.7 131.9 205.5 236.0 265.3 285.0 301.2 311.02014 53.7 117.2 189.9 210.7 233.4 251.6 263.92015 45.2 124.0 175.3 195.4 223.4 258.62016 30.9 83.5 144.6 166.2 193.42017 40.5 98.2 141.0 169.32018 27.0 105.6 133.92019 33.8 73.12020 28.6

Total $ 1,710.0

Alloutstandingliabilitiesfor2012andsubsequentyears,netofreinsurance $ 431.4Alloutstandingliabilitiesbefore2012,netofreinsurance(unaudited) —

Liabilitiesforclaimsandclaimadjustmentexpenses,netofreinsurance $ 431.4

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Financial and Professional Insurance LinesIncurred Claims, IBNR and Loss Adjustment Expenses, Net of Reinsurance As at December 31, 2020

Total of IBNR PlusExpected

Development onReported Claims

Cumulative Numberof Reported Claims

For the Years Ended December 31,Unaudited Prior Years

Accident Year 2012 2013 2014 2015 2016 2017 2018 2019 2020

$ (in millions)2012 88.9 90.2 94.1 97.7 94.6 90.1 102.5 97.3 103.3 10.5 5752013 106.7 101.4 105.6 102.5 101.7 92.5 91.5 97.7 9.2 5672014 136.5 132.8 131.5 121.7 133.1 122.1 120.0 9.1 7912015 176.1 177.4 187.4 191.8 193.2 182.2 16.8 1,0852016 193.3 213.9 218.7 204.3 182.1 26.2 1,2492017 208.8 185.3 190.0 181.7 21.2 1,7202018 159.8 175.8 151.7 27.2 4,6442019 252.0 245.5 102.6 23,7612020 352.9 261.7 69,692

Total $ 1,617.1

Financial and Professional Insurance LinesCumulative Paid Claims and Allocated Loss Adjustment Expenses, Net of Reinsurance

For the Years Ended December 31, Unaudited Prior Years

Accident Year 2012 2013 2014 2015 2016 2017 2018 2019 2020 ($ in millions)2012 22.8 39.7 50.9 59.6 65.5 70.8 80.6 85.8 91.52013 8.2 21.6 31.7 66.1 64.6 73.5 75.5 78.82014 3.0 31.0 54.3 73.1 80.6 86.7 93.32015 13.9 43.8 70.5 90.0 110.9 140.12016 15.5 71.8 103.2 131.2 127.32017 27.3 51.5 83.9 118.32018 21.3 76.2 102.72019 27.6 87.62020 48.2

Total $ 887.8

Alloutstandingliabilitiesfor2012andsubsequentyears,netofreinsurance $ 729.3Alloutstandingliabilitiesbefore2012,netofreinsurance(unaudited) 9.2

Liabilitiesforclaimsandclaimadjustmentexpenses,netofreinsurance $ 738.5

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Property Catastrophe and Other Property ReinsuranceIncurred Claims, IBNR and Loss Adjustment Expenses, Net of Reinsurance As at December 31, 2020

Total of IBNR PlusExpected

Development onReported Claims

Cumulative Numberof Reported Claims

For the Years Ended December 31,Unaudited Prior Years

Accident Year 2012 2013 2014 2015 2016 2017 2018 2019 2020

$ (in millions)2012 282.2 305.5 288.2 281.0 284.4 281.4 273.8 263.7 267.0 6.8 6742013 221.9 204.5 194.4 183.0 181.5 178.0 175.1 172.3 3.5 8292014 193.5 181.4 165.1 153.7 154.1 149.1 149.0 2.0 9022015 218.7 191.1 181.0 160.0 175.2 175.3 5.9 1,0442016 277.9 277.5 275.4 253.4 249.5 2.3 1,2962017 563.9 539.8 520.6 509.3 7.5 1,9522018 360.5 422.6 420.0 8.9 1,8132019 286.4 293.8 4.2 1,3352020 328.0 161.7 876

$ 2,564.2

Property Catastrophe and Other Property ReinsuranceCumulative Paid Claims and Allocated Loss Adjustment Expenses, Net of Reinsurance

For the Years Ended December 31,Unaudited Prior Years

Accident Year 2012 2013 2014 2015 2016 2017 2018 2019 2020 ($ in millions)2012 35.9 137.1 190.5 210.8 218.4 229.6 234.0 244.1 249.92013 35.0 101.0 150.3 162.8 167.7 169.2 170.8 165.22014 38.0 103.0 130.2 140.6 144.7 143.5 145.22015 36.1 96.8 129.6 142.0 159.1 161.52016 57.6 167.4 209.2 220.7 234.42017 123.8 359.9 419.9 444.52018 123.7 331.5 352.32019 28.4 161.72020 43.0

Total $ 1,957.7

Alloutstandingliabilitiesfor2012andsubsequentyears,netofreinsurance 606.5Alloutstandingliabilitiesbefore2012,netofreinsurance(unaudited) 24.5

Liabilitiesforclaimsandclaimadjustmentexpenses,netofreinsurance $ 631.0

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Casualty ReinsuranceIncurred Claims, IBNR and Loss Adjustment Expenses, Net of Reinsurance As at December 31, 2020

Total of IBNR PlusExpected

Development onReported Claims

Cumulative Numberof Reported Claims

For the Years Ended December 31,Unaudited Prior Years

Accident Year 2012 2013 2014 2015 2016 2017 2018 2019 2020

$ (in millions)2012 237.0 235.3 246.7 238.3 235.3 236.2 244.9 247.2 221.6 — 1,8042013 217.7 233.0 228.8 226.1 208.8 203.7 206.5 176.5 3.7 1,6792014 209.0 212.4 221.1 214.5 207.7 210.2 173.4 0.3 1,7752015 198.0 205.4 214.6 216.9 214.5 171.4 4.9 1,9062016 237.7 250.6 250.4 260.3 220.9 18.7 1,9372017 249.9 247.3 258.2 201.5 25.0 1,7712018 233.0 262.9 209.2 70.5 1,4882019 239.0 189.4 102.6 9632020 259.3 235.2 342

Total $ 1,823.2

Casualty ReinsuranceCumulative Paid Claims and Allocated Loss Adjustment Expenses, Net of Reinsurance

For the Years Ended December 31,Unaudited Prior Years

Accident Year 2012 2013 2014 2015 2016 2017 2018 2019 2020 ($ in millions)2012 2.2 17.9 42.3 65.9 97.1 118.6 135.7 145.4 163.32013 3.5 16.0 43.2 65.5 93.8 115.9 128.7 140.92014 2.6 14.1 38.2 60.9 87.4 108.7 127.12015 3.6 18.4 39.1 66.3 90.4 109.92016 9.5 34.2 65.4 97.7 128.22017 9.1 31.1 59.8 98.72018 7.3 34.0 74.22019 9.4 36.92020 9.4

Total $ 888.6

Alloutstandingliabilitiesfor2012andsubsequentyears,netofreinsurance 934.6Alloutstandingliabilitiesbefore2012,netofreinsurance(unaudited) 149.6

Liabilitiesforclaimsandclaimadjustmentexpenses,netofreinsurance $ 1,084.2

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Specialty ReinsuranceIncurred Claims, IBNR and Loss Adjustment Expenses, Net of Reinsurance As at December 31, 2020

Total of IBNR PlusExpected

Development onReported Claims

Cumulative Numberof Reported Claims

For the Years Ended December 31,Unaudited Prior Years

Accident Year 2012 2013 2014 2015 2016 2017 2018 2019 2020

$ (in millions)2012 179.5 202.9 192.2 176.9 175.4 175.9 172.7 170.1 166.6 0.1 6362013 148.4 143.4 135.0 123.0 122.2 118.4 117.9 114.2 0.5 5752014 155.3 143.0 135.1 125.8 128.8 127.1 120.3 — 6242015 168.9 173.8 168.4 162.7 160.9 152.9 5.2 7652016 242.1 243.3 241.0 233.1 222.8 9.7 9232017 384.2 396.7 380.2 359.3 11.3 1,3112018 401.7 401.0 391.7 23.0 1,3722019 480.0 495.0 62.4 1,4332020 418.1 173.4 1,096

Total $ 2,440.9

Specialty ReinsuranceCumulative Paid Claims and Allocated Loss Adjustment Expenses, Net of Reinsurance

For the Years Ended December 31,Unaudited Prior Years

Accident Year 2012 2013 2014 2015 2016 2017 2018 2019 2020 ($ in millions)2012 25.3 95.6 131.1 141.2 146.6 152.0 153.3 156.1 156.62013 25.7 73.5 89.7 97.1 104.2 104.2 105.2 104.92014 17.1 58.1 83.3 91.4 102.0 104.9 106.62015 18.1 57.9 106.1 124.8 134.0 137.02016 59.1 152.6 167.7 185.9 196.22017 95.3 240.8 273.4 309.32018 27.9 282.8 317.42019 275.4 384.82020 213.6

Total $ 1,926.4

Alloutstandingliabilitiesfor2012andsubsequentyears,netofreinsurance 514.5Alloutstandingliabilitiesbefore2012,netofreinsurance(unaudited) 20.9

Liabilitiesforclaimsandclaimadjustmentexpenses,netofreinsurance $ 535.4

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Reconciliation of Incurred and Paid Claims Development to total Provision for Losses and LAETwelve Months Ended December 31,

2020Twelve Months Ended

December 31, 2019 ($ in millions)Netoutstandingliabilities:

Insurancelines-Propertyinsurancelines 226.8 190.7-Casualtyinsurancelines 618.7 669.2-Marine,aviationandenergyinsurancelines 431.4 591.5-Financialandprofessionalinsurancelines 738.5 657.4

Totalinsurancelines 2,015.4 2,108.8

Reinsurancelines-Propertycatastropheandotherpropertyreinsurance 631.0 528.6-Casualtyreinsurance 1,084.2 1,602.2-Specialtyreinsurance 535.4 575.9

Totalreinsurancelines 2,250.6 2,706.7

NetlossandLAE 4,266.0 4,815.5

Reinsurancerecoverableonunpaidlosses:Insurancelines 2,140.3 1,772.8Reinsurancelines 1,054.9 547.0

Totalreinsurancerecoverableonunpaidlosses 3,195.2 2,319.8

Unallocatedclaimsincurred 50.3 44.0Otherreinsurancebalancesrecoverable (346.7) (227.4)Other 0.5 (0.1)

(295.9) (183.5)

ProvisionforlossesandLAEattheendoftheyear 7,165.3 6,951.8

____________________

Otherreinsurancebalancesrecoverableprimarilyincludeamountsthathavebeenbilledbutnotyetreceived.

Average Annual Percentage Payout of Incurred Claims by Age, Net of Reinsurance

Years 1 2 3 4 5 6 7 8 9

Insurance 16.3% 26.7% 16.1% 12.6% 8.4% 6.9% 4.6% 2.0% 2.0%

Reinsurance 18.0% 31.6% 15.6% 9.5% 8.6% 5.3% 4.0% 2.5% 3.8%

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11.Income TaxesAspenHoldingsandAspenBermudaareincorporatedunderthelawsofBermuda.UnderBermudalaw,thecorporatetaxrateiszeroand,asaresult,Aspen

Holdings and Aspen Bermuda are not taxed on any Bermudian income or capital gains. In the event of any Bermudian income or capital gains taxes beingimposed,AspenHoldingsandAspenBermudahavereceivedanundertakingfromtheBermudaMinisterofFinancethatsuchentitieswillbeexemptfromthosetaxesuntilMarch31,2035.

TheCompany’sU.S.operatingcompaniesweresubjecttoaU.S.federalincometaxrateof21%.TheCompany’sU.K.operatingcompaniesaretaxedattheU.K.corporatetaxrateof19%.Totalincometax(benefit)/expenseforthetwelvemonthsendedDecember31,2020,2019and2018wasallocatedasfollows:

Twelve Months Ended December 31, 2020 2019 2018 ($ in millions)Incometaxexpense/(benefit)allocatedtonetloss $ 8.6 $ 22.9 $ (10.2)Incometaxexpense/(benefit)allocatedtoothercomprehensiveincome 6.2 11.2 4.1Totalincometaxexpense/(benefit) $ 14.8 $ 34.1 $ (6.1)

(Loss)/income from operations before income taxes and income tax expense/(benefit) attributable to that (loss)/income for the twelve months endedDecember31,2020,2019and2018isprovidedinthetablesbelow: Twelve Months Ended December 31, 2020

(Loss)/income before tax

Current tax (benefit)/expense

Deferred tax (benefit)/expense

Total income tax (benefit)/expense

($ in millions)Bermuda $ (77.6) $ — $ — $ —U.S. 19.7 8.9 (5.7) 3.2U.K. 12.4 0.1 — 0.1Other 14.0 5.3 — 5.3Total $ (31.5) $ 14.3 $ (5.7) $ 8.6

Twelve Months Ended December 31, 2019

(Loss) before tax

Current tax (benefit)/expense

Deferred tax (benefit)/expense

Total income tax (benefit)/expense

($ in millions)Bermuda $ (107.6) $ — $ — $ —U.S. (60.0) 1.0 6.5 7.4U.K. (45.7) (6.7) 17.3 10.6Other (5.5) 4.0 0.9 4.9Total $ (218.8) $ (1.7) $ 24.7 $ 22.9

Twelve Months Ended December 31, 2018(Loss)

before taxCurrent tax

(benefit)/expenseDeferred tax

(benefit)/expenseTotal income tax (benefit)/expense

($ in millions)Bermuda $ (72.1) $ — $ — $ —U.S. (81.0) 6.1 (8.1) (2.0)U.K. (4.7) (12.2) (0.1) (12.3)Other 1.8 4.4 (0.3) 4.1Total $ (156.0) $ (1.7) $ (8.5) $ (10.2)

________________TheU.S.currenttaxexpenseincludes$4.5millionofprioryearadjustments.

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The U.S. deferred tax benefit of $5.7 million is an intraperiod tax allocation between the IncomeStatement and unrealized gains on investments in othercomprehensiveincome.

Currenttaxexpensein“other”ispredominantlymadeupoftaxationpaidinrespectofbranchesofU.K.andBermudianoperatingsubsidiariesandwithholdingtaxespayableinAustralia.

As noted above, the tax rate in Bermuda, the Company’s country of domicile, is zero. Application of the statutory tax rate for operations in otherjurisdictions produces a differential to the expected income tax (benefit)/expense as shown in the table below. The reconciliation between the income taxexpense/(benefit)andtheamountthatwouldresultfromapplyingthestatutoryratefortheCompanyforthetwelvemonthsendedDecember31,2020,2019and2018isprovidedinthetablebelow: Twelve Months Ended December 31, 2020 2019 2018Income Tax Reconciliation ($ in millions)Incometaxbenefitatstatutorytaxrateofzeropercent $ — $ — $ —Overseasstatutorytaxratesdifferential 12.1 (21.2) (17.1)Baseerosionandanti-abusetax(BEAT)expense 4.3 0.3 6.0Prioryearadjustments (3.2) (1.7) 1.4Changeinvaluationallowance (10.4) 42.6 7.1Impactofunrecognizedtaxbenefits — — (12.8)Restrictedforeigntaxcredits — 1.5 —Australiannon-residentwithholdingtax 1.0 1.0 4.4Share-basedpayments — (0.6) 0.2Foreignexchange 1.9 — 0.1Non-deductibleexpenses 4.6 — 0.7Non-taxableitems — (0.1) (0.3)Impactofchangesinstatutorytaxrates (1.7) 1.1 0.1

Totalincometaxexpense/(benefit) $ 8.6 $ 22.9 $ (10.2)

________________The submission dates for filing income tax returns for the Company’s U.S. and U.K. operating subsidiaries are after the submission date of this report.

Accordingly,thefinaltaxliabilitiesmaydifferfromtheestimatedtaxexpenseincludedinthisreportandmayresultinprioryearadjustmentsbeingreported.Theprior period adjustments for the twelve months ended December 31, 2020predominantly relate to the determination of the results of the branches of the U.K.operatingsubsidiaries.ThepriorperiodadjustmentsforthetwelvemonthsendedDecember31,2019and2018predominantlyrelatetothedeterminationofresultsunderU.K.GAAPuponwhichtheU.K.taxreturnsarebased.Theseitemscanonlybeultimatelydeterminedafterthisreportisfiled.

The2020valuationallowanceincludesa$20.9millionreductionresultingfromU.S.currentyearincome,ofwhich$14.0millionrelatestotheutilizationofexistingnetoperatinglosses,anda$10.4millionincreaserelatingtodeferredtaxassetsinU.K.operatingsubsidiaries.The2019valuationallowanceincludes$9.9millionrelatingtothelossesincurredbytheU.S.branchofAspenU.K.and$28.2millionrelatingtodeferredtaxassetsinU.K.subsidiaries.

In2020,thecompanydidnothaveanyunrecognizedtaxbenefits.In2018,the$12.8millionbenefitrelatestothesuccessfulconclusionofaU.K.taxinquirywhichenabledthereleaseofaprovisionwehadbeenholdingagainstthepotentialdisallowanceofaprioryearadjustment.

Income tax returns that have been filed by the Company’s U.S. operating subsidiaries are subject to examination for 2016 and later tax years. TheCompany’sU.K.operatingsubsidiaries’incometaxreturnsaresubjecttoexaminationfor2019andlatertaxyears.

RestrictedforeigntaxcreditsaretaxespaidbybranchesofU.K.operatingsubsidiariesthatarenotcreditableagainstU.K.taxes.

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ThetaxeffectsoftemporarydifferencesandcarryforwardsthatgiverisetodeferredtaxassetsanddeferredtaxliabilitiesarepresentedinthefollowingtableasatDecember31,2020and2019:

As at December 31, 2020 2019 ($ in millions)Deferred tax assets:

Share-basedpayments $ — $ 0.3Operatinglosscarryforwards 119.6 121.5Insurancereserves:Lossesandlossadjustmentexpenses 7.9 5.0Accruedexpenses 6.4 7.1Insurancereserves:Unearnedpremiums 17.6 15.3Deferredpolicyacquisitioncosts — 0.1Officepropertiesandequipment 12.7 16.8Operatingleaseliabilities 17.7 21.5Othertemporarydifferences 2.5 6.1

Total deferred tax assets 184.4 193.7Lessvaluationallowance (138.9) (149.2)

Deferred tax assets, net of valuation allowance $ 45.5 $ 44.5

Deferred tax liabilities:

Unrealized(gains)oninvestments (2.7) (2.7)Intangibleassets (20.1) (1.6)Deferredpolicyacquisitioncosts (8.4) (16.4)Right-of-useoperatingleaseassets (12.3) (19.9)Othertemporarydifferences (2.0) (3.9)

Total deferred tax (liabilities) (45.5) (44.5)

Net deferred tax assets $ — $ —

DeferredtaxliabilitiesandassetsrepresentthetaxeffectoftemporarydifferencesbetweenthevalueofassetsandliabilitiesforfinancialstatementpurposesandsuchvaluesasmeasuredbyU.K.,U.S.andothertaxlawsandregulations.

Inassessingtherealizabilityofdeferredtaxassets,managementconsiderswhetheritismorelikelythannotthatsomeportionorallofthedeferredtaxassetswillnotberealized.Theultimaterealizationofdeferredtaxassetsisdependentuponthegenerationoffuturetaxableincomeduringtheperiodsinwhichthosetemporarydifferencesandcarryforwardsbecomedeductibleorcreditable.Managementconsidersthescheduledreversalofexistingtaxabletemporarydifferences,carrybackavailability,projectedfuturetaxableincome,andtax-planningstrategiesinmakingthisassessment.

Asat December 31, 2020, the Companyhas net operating losses carryforwards for U.S. federal incometax purposes of $501.7 million (2019—$606.8million)andnetoperatinglossescarryforwardsforU.K.corporatetaxpurposesof$99.5million(2019—$93.2million).Ofthe$501.7millionthatareavailabletooffsetfutureU.S.federaltaxableincome,$444.3millionwillexpirebetween2030and2039and$57.4millionareavailabletooffsetfutureU.S.federaltaxableincomeoveranindefiniteperiod.Theamountofpre-mergernetoperatinglossescarryforwardsthatcanbeusedeachyearislimitedbys382to$6.5millionforAspenU.K.’sU.S.businessand$20.8millionfortheU.S.operatingsubsidiaries.

The U.K. net operating losses are available to offset future U.K. corporate income over an indefinite period. For U.S. federal income tax purposes, theCompanyalsohascapitallosscarryforwardsof$Nil(2019—$0.5million)andcharitablecontributioncarryforwardsof$1.0million(2019—$1.1million)withexpiryperiodsbetween2021and2025.ForU.K.corporatetaxpurposes,theCompanyhascapitallosscarryforwardsof$3.8millionwhichareavailabletooffsetfutureU.K.capitalgainsoveranindefiniteperiod.

A valuation allowance of $113.9 million (2019 — $134.8 million*) on U.S. deferred tax assets (which includes these loss carryforwards) has beenrecognizedatDecember31,2020asmanagementbelievesthatitismorelikelythannotthatatax

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benefitwillnotberealized.Thedecreaseinthisportionofthevaluationallowancetotals$20.9million(2019—$9.2millionincrease)with$20.9million(2019—$9.2millionincrease)recordedintheconsolidatedincomestatement.

Avaluationallowanceof$24.8million(2019—$14.4million*)hasbeenestablishedagainstU.K.deferredtaxassets.Theincreaseinthisportionofthevaluationallowancetotals$10.4million(2019—$28.2million)with$10.4million(2019—$28.2millionincrease)recordedintheconsolidatedincomestatementand $Nil (2019 —$Nil) recorded in other comprehensive income. The U.K. and U.S. valuation allowance combined total is $138.9 million (2019 —$149.2million).

*Theprioryearcomparativefigureshavebeenre-presentedtoalignwiththecurrentyearsgeographicalsplits.

12. Capital StructureThefollowingtableprovidesasummaryoftheCompany’sauthorizedandissuedsharecapitalasatDecember31,2020and2019:

As at December 31, 2020 At December 31, 2019

Number$ in

Thousands Number$ in

ThousandsAuthorizedsharecapital:

OrdinaryShares$0.01pershare(2019—$0.01pershare 70,000,000 700 70,000,000 700PreferenceShares0.15144558¢pershare 30,000,000 45 30,000,000 45

Totalauthorizedsharecapital 745 745

Issuedsharecapital:Issuedordinaryshares$0.01pershare(2019—$0.01pershare 60,395,839 604 60,395,839 604Issued5.950%preferencesharesof0.15144558¢eachwithaliquidationpreferenceof$25pershare 11,000,000 17 11,000,000 17Issued5.625%preferencesharesof0.15144558¢eachwithaliquidationpreferenceof$25pershare 10,000,000 15 10,000,000 15Issued5.625%preferencesharesof0.15144558¢representedbydepositaryshares,eachwithaliquidationpreferenceof$25pershare 10,000 — 10,000 —

Totalissuedsharecapital 636 636

______________Eachdepositarysharerepresentsa1/1000 interestinashareofthe5.625%preferenceshares.

(a) Ordinary SharesIssued Ordinary Shares. TheCompany’sissuedordinarysharesofparvalue$0.01atbothDecember31,2020and2019was60,395,839.TheCompanydid

notacquireanyordinarysharesforthetwelvemonthsendedDecember31,2020.

(b) Preference SharesPreference Shares Issuance.OnMay2, 2013, weissued11,000,0005.950%Fixed-to-FloatingRatePerpetual Non-CumulativePreferenceShares, witha

liquidationpreferenceof$25pershare(the“5.950%PreferenceShares”)foranaggregateamountof$275.0million.Our5.950%PreferenceSharesarelistedontheNYSEundersymbol“AHLPRC.”

OnSeptember20,2016,theCompanyissued10,000,000sharesof5.625%PerpetualNon-CumulativePreferenceShares(the“5.625%PreferenceShares”).The5.625%PreferenceShareshavealiquidationpreferenceof$25pershare.Netproceedswere$241.3million,consistingof$250.0millionoftotalliquidationpreferenceless$8.7millionofissuanceexpenses.The5.625%PreferenceSharesarelistedontheNYSEunderthesymbol“AHLPRD”.

OnAugust13,2019,theCompanyissued10,000,000depositaryshares,eachofwhichrepresents1/1000 interestinashareofthenewlydesignated5.625%PerpetualNon-CumulativePreferenceShares.Thedepositaryshareshavealiquidationpreferenceof$25pershare.Netproceedswere$241.6million,comprising$250.0millionoftotalliquidationpreferenceless$8.4millionofissuanceexpenses.ThedepositarysharesarelistedontheNYSEunderthesymbol“AHLPRE”.

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(c) Additional Paid-in CapitalAdditionalpaid-incapitalasatDecember31,2020was$1,469.7million(December31,2019—$1,201.7million).Includedwithinadditionalpaid-incapital

is theaggregate liquidation preferences of the Company’s preference shares of $775.0million less issuecosts of $21.5million (December 31, 2019—$775.0millionlessissuecostsof$21.5million.

Duringthefourthquarterof2020,ourparentcompanyHighlandsBermudaHoldco,Ltd.contributedadditionalcapitaltotaling$268.0million.

13.Statutory Requirements and Dividends Restrictions

Asaholdingcompany,AspenHoldingsreliesondividendsandotherdistributionsfromitsOperatingSubsidiariestoprovidecashflowtomeetongoingcashrequirements, includinganyfuturedebt service payments andother expenses, andtopaydividends, if any, to ourpreferenceandordinaryshareholders. AspenHoldingsmust complywiththeprovisionsoftheBermudaCompaniesAct1981,asamended,(the“CompaniesAct”) regulatingthepaymentofdividendsanddistributions. As at December 31, 2020, there were no restrictions under Bermuda law or the law of any other jurisdiction on the payment of dividends fromretainedearningsbyAspenHoldings.

TheabilityoftheCompany’sOperatingSubsidiariestopaytheCompanydividendsorotherdistributionsissubjecttothelawsandregulationsapplicabletoeachjurisdiction,aswellastheOperatingSubsidiaries’needtomaintaincapitalrequirementsadequatetomaintaintheirinsuranceandreinsuranceoperationsandtheirfinancialstrengthratingsissuedbyindependentratingagencies.

The company law of England and Wales prohibits Aspen U.K. or AULfromdeclaring a dividend to its shareholders unless it has “profits available fordistribution.” Thedetermination of whether a companyhas profits available for distribution is basedonits accumulated realized profits andother distributablereserveslessitsaccumulatedrealizedlosses.WhiletheU.K.insuranceregulatorylawsimposenostatutoryrestrictionsonageneralinsurer’sabilitytodeclareadividend,therulesofthePrudentialRegulationAuthority(the“PRA”)requireeachinsurancecompanywithinitsjurisdictiontomaintainitssolvencymarginatalltimes.Accordingly,AspenU.K.,AMALandAULmaynotpayadividendifthepaymentofsuchdividendwouldresultintheirSCRcoverageratiofallingbelowcertainlevels.Inaddition,anyfuturechangesregardingregulatoryrequirements,includingthosedescribedabove,mayrestricttheabilityofAspenU.K.,AMALandAULtopaydividendsinthefuture.AsatDecember31,2020,AspenU.K.hadanaccumulatedbalanceofretainedlossesofapproximately$200.3millionandAUL had an accumulated balance of retained losses of approximately £73.1 million. Aspen U.K. held a capital contribution reserve of $555.0 million as atDecember31,2020which,undercertaincircumstances,couldbedistributable.

AspenBermudamust complywiththeprovisionsof theCompanies Act regulatingthepayment of dividendsanddistributions. TherewerenosignificantrestrictionsundercompanylawontheabilityofAspenBermudatopaydividendsfundedfromitsaccumulatedbalancesofretainedincomeasatDecember31,2020.AspenBermudamaynotinanyfinancialyearpaydividendswhichwouldexceed25%ofitstotalstatutorycapitalandsurplus,asshownonitsstatutorybalancesheetinrelationtothepreviousfinancialyear,unlessitfileswiththeBMAasolvencyaffidavitatleastsevendaysinadvance.AsatDecember31,2020,25% of Aspen Bermuda’s statutory capital and surplus amounted to $286.9 million. Aspen Bermuda must also obtain the prior approval of the BMAbeforereducingitstotalstatutorycapitalassetoutinitspreviousyear’sfinancialstatementsby15%ormore.

UnderbothNorthDakotaandTexaslaw,insurancecompaniesmayonlypaydividendsoutofearnedsurplusasdistinguishedfromcontributedsurplus.Assuch,AspenSpecialtyandAAICcouldnotpayadividendasatDecember31,2020.

ActualandrequiredstatutorycapitalandsurplusfortheprincipaloperatingsubsidiariesoftheCompany,excludingitsLloyd’ssyndicate,asatDecember31,2020andDecember31,2019wereestimatedasfollows: As at December 31, 2020 U.S. Bermuda U.K. ($ in millions)Requiredstatutorycapitalandsurplus $ 504.8 $ 632.5 $ 786.0Actualstatutorycapitalandsurplus $ 606.2 $ 1,147.5 $ 969.5

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As at December 31, 2019 U.S. Bermuda U.K. ($ in millions)Requiredstatutorycapitalandsurplus $ 404.0 $ 788.4 $ 782.0Actualstatutorycapitalandsurplus $ 502.0 $ 1,380.6 $ 841.9

AsthesolecorporatememberofourLloyd’sSyndicate,AULwasrequiredtomaintainFundsatLloyd’sof$815.8millionasatDecember31,2020.AsatDecember31,2020,AULhadtotalfundsatLloyd’sof$758.8millionofwhich$503.3millionwasprovidedbyAspenBermuda.

The Bermuda Monetary Authority is the group supervisor of the Company. The laws and regulations of Bermuda require that the Company maintain aminimumamountofgroupstatutorycapitalandsurplusbasedontheenhancedcapitalrequirementusingthegroupstandardizedrisk-basedcapitalmodeloftheBermuda Monetary Authority. The Company is also subject to an early-warning level based on 181%of the enhanced capital requirement which may triggeradditionalreportingrequirementsorotherenhancedoversight.ThestatutorycapitalrequirementsofourOperatingSubsidiariesaresetoutabove.Totheextentthattheserequirementsaremet,wedonotanticipateanydividendrestrictionsarisingasaresultoftheCompany’senhancedcapitalrequirement.FormoreinformationontheCompany’sregulatoryrequirements,refertoItem4,“InformationontheCompany—RegulatoryMatters”above.

14. Dividends

Dividends.OnMarch4,2021,theCompany’sBoardofDirectorsdeclaredthefollowingdividends:Dividend Payable on: Record Date:

5.950%PreferenceShares(AHLPRC) $ 0.3719 April1,2021 March15,20215.625%PreferenceShares(AHLPRD) $ 0.3516 April1,2021 March15,20215.625%PreferenceShares,representedbydepositaryshares(AHLPRE) $ 351.56 April1,2021 March15,2021

______________Thenewly-designated5.625%PreferenceSharesarerepresentedbydepositaryshares,eachrepresentinga1/1000 interestinashareofthe5.625%

PreferenceShares.Thedividendpaidperdepositaryshareislikewise1/1000 ofthedeclareddividend,equivalentto$0.35156perdepositaryshare.

15.Retirement PlansTheCompanyoperatesdefinedcontributionretirementplansforthemajorityofitsemployeesatvaryingratesoftheirsalariesuptoamaximumof20.0%.

TotalcontributionsbytheCompanytotheretirementplanswere$12.1millioninthetwelvemonthsendedDecember31,2020(2019—$12.9million,2018—$16.0million).

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16. Share-Based Payments and Long-Term Incentive PlanIn2019,theCompanyimplementedanewlong-termincentivescheme,underwhichannualawardsaresplit equallybetweenPerformanceUnitsandExit

Units. Performance Units vest after two years subject to the Company achieving pre-determined growth in book value per share targets. Exit Units vest uponchangeofcontrol(SaleorIPO)andachievingpre-determinedmultipliesofinvestedcapitalreturntargets.BothPerformanceUnitsandExitUnitsarecash-basedawards.

The Company’s total share-based compensation / long-term incentive plan expense for the twelve months ended December 31, 2020 was $2.1 million(December31,2019—$3.5million),whichprimarilyrelatedtoachargeof$1.3million(December31,2019—$0.8million)inrelationtoPerformanceUnits,$0.5million(December31,2019—$0.8million)inrelationtopreviouslyawardeddeferredcashawardsand$0.3million(December31,2019—$1.9million)inrelationtoothershare-basedcompensationexpense.Theincometaxeffectofthisisnotconsideredtobematerial.

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17. Intangible Assets and GoodwillThefollowingtableprovidesasummaryoftheCompany’sintangibleassetsforthetwelvemonthsendedDecember31,2020and2019:

Twelve Months Ended December 31, 2020 Beginning of the Year Additions/(Disposals) Amortization Impairment End of the Year ($ in millions)IntangibleAssetsTrademarks $ 1.9 $ — $ (0.3) $ — $ 1.6AgencyRelationships 1.2 — (0.6) — 0.6Non-competeAgreements 0.2 — (0.2) — —InsuranceLicenses 16.7 — — — 16.7Goodwill 3.9 — — — 3.9Total $ 23.9 $ — $ (1.1) $ — $ 22.8

Twelve Months Ended December 31, 2019 Beginning of the Year Additions/(Disposals) Amortization Impairment End of the Year ($ in millions)IntangibleAssetsTrademarks $ 2.5 $ — $ (0.6) $ — $ 1.9AgencyRelationships 1.8 — (0.6) — 1.2RenewalRights 1.0 — (0.1) (0.9) —Non-competeAgreements 0.4 — (0.2) — 0.2InsuranceLicenses 16.7 — — — 16.7Goodwill 3.9 — — — 3.9Total $ 26.3 $ — $ (1.5) $ (0.9) $ 23.9

Aspen’sintangibleassetsrelatetotrademarks, contractstosell productsthroughindependentbrokerandagents(AgencyRelationships), anagreementforrenewalrightswithLibertySpecialtyMarketsLimited,non-competeagreementsandlicensestotradeintheU.S.andU.K.

Inaddition,Aspenhasrecognizedgoodwillof$2.1millionontheacquisitionofequityvotinginterestofBlueWaters,aspecialistmarineinsuranceagencyinOctober2016andof$1.8milliononthepurchaseinJanuary2017of49%shareofDigitalRe,adigitalriskandspecialtyinsurer.

The“Aspen” trademark, valued at $1.4 million, goodwill and insurance licenses are considered to have an indefinite life and are tested annually forimpairmentorwheneventsorchangesincircumstancesindicatethattheseassetsmightbeimpaired.FortheyearsendedDecember31,2020andDecember31,2019,theCompanyperformeditsannualqualitativeassessmentanddeterminedthatitwasnotmorelikelythannotthatthesewereimpaired.

Theremainingintangibleassets,includingthe“BlueWaters”trademarkvaluedat$0.2million,wereestimatedtohaveaneconomicusefullifeof5years.TheCompanyamortizestheestimatedvalueoftheseassetsovertheirestimatedusefullifewhichisincludedasanexpenseintheincomestatement.

18. Operating LeasesAsatDecember31,2020,theCompanyhasrecognizedright-of-useoperatingleaseassetsof$74.1million,netofimpairmentandoperatingleaseliabilities

of$106.0million.Right-of-useoperatingleaseassetscompriseprimarilyofleasedofficerealestategloballyandotherassets.Forallofficerealestateleases,rentincentives, includingreduced-rentandrentfreeperiodsandcontractuallyagreedrentincreasesduringtheleaseterm,havebeenincludedwhendeterminingthepresentvalueoffuturecashflows.

AspartoftheCompany’soperatingeffectivenessandefficiencyprogram,weareconsolidatingourofficespace.Wherenegotiationsareeitherinadvancedstagesofdiscussionanditisprobablethatthesub-leasetransactionswillbecompleted,orwehaveagreedtermstosub-leaseourofficespace,wehaveassessedourright-of-useleaseassetsforimpairmentandhaverecognizeda$12.9million(2019—$12.3million)chargewithintheperiod.

TheCompanybelievesitsofficespaceissufficienttoconductitsoperationsfortheforeseeablefutureintheselocations.TheCompanyhasnoleasetransactionsbetweenrelatedparties.

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Operating lease charge.ThefollowingtablesummarizestheoperatingleasechargeforthetwelvemonthsendedDecember31,2020and2019:For the Twelve Months Ended

December 31, 2020 December 31, 2019 ($ in millions)Amortizationchargeonright-of-useoperatingleasedassets $ 11.8 $ 13.4Interestonoperatingleaseliabilities 5.5 4.6Operatingleasecharge $ 17.3 $ 18.0

Lease Liabilities.Thefollowingtablesummarizesthematurityofleaseliabilitiesundernon-cancellableleasesasofDecember31,2020and2019:December 31, 2020 December 31, 2019

($ in millions)Operatingleases—maturities

2020 $ — $ 17.72021 17.2 16.42022 14.2 13.02023 13.5 12.22024 12.6 11.72025 12.2 11.5Lateryears 63.4 62.1

Totalminimumleasepayments $ 133.1 $ 144.6Lessimputedinterest (27.1) (31.4)Totalleaseliabilities $ 106.0 $ 113.2

Other lease information.ThefollowingtablesummarizesthecashflowsonoperatingleasesforthetwelvemonthsendedDecember31,2020and2019,andothersupplementalinformation:

For the Twelve Months EndedDecember 31, 2020 December 31, 2019

($ in millions)Cashpaidforamountsincludedinthemeasurementofleaseliabilities-Operatingcashoutflowfromoperatingleases $ (17.3) $ (18.0)

Right-of-useassetsobtainedinexchangeforleaseobligations-Operatingleases $ 5.0 $ 37.3

ReductiontoRight-of-useassetsresultingfromreductionstoleaseobligations-Operatingleases $ 13.0 $ 6.1

WeightedAverages-Operatingleases,remainingleaseterms(years) 9.1 10.1-Operatingleases,averagediscountrate 5.0% 5.0%

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19. Related Party Transactions

Apollo’sindirect subsidiary,ApolloAssetManagementEuropePCLLP(“AAME”),servesastheinvestmentmanagerfortheCompanyandcertainoftheCompany’s subsidiaries, and Apollo’s indirect subsidiary, Apollo Management Holdings, L.P. (“AMH”), provides the Company with management consultingservicesandadvisoryservices.

Additionally,certainemployeesofApolloanditsaffiliatesserveontheBoard.

A description of relationships we have with Apollo and its affiliates and transactions that have existed or that we have entered into with Apollo and itsaffiliatesaredescribedbelow.

Investment Management Relationships

AAMEservesastheCompany’sinvestmentmanagerandtheinvestmentmanagerforcertainofoursubsidiaries,andprovidescentralizedassetmanagementinvestmentadvisoryandriskservicesfortheportfolioofourinvestmentsandinvestmentsofsuchsubsidiariespursuanttotheinvestmentmanagementagreements(“IMAs”)thathavebeenenteredintowithAAME.

Inaddition,pursuanttotheIMAs,AAMEmayengagesub-advisorsordelegatestoprovidecertainoftheinvestmentadvisoryandmanagementservicestooursubsidiaries.Suchsub-advisorsmayincludeaffiliatesofAAME.

UndereachoftheIMAs,AAMEwillbepaidanannualinvestmentmanagementfee(the“ManagementFee”)whichwillbebasedonacost-plusstructure.The“cost”iscomprisedofthedirectandindirectfees,costs,expensesandotherliabilitiesarisinginorotherwiseconnectedwiththeservicesprovidedundertheIMAs.The“plus”componentwillbeamark-upinanamountofupto25%determinedbasedonanapplicabletransferpricingstudy.TheManagementFeewillbesubjecttocertainmaximumthresholdlevels,includinganannualfeecapof15bpsofthetotalamountofinvestableassets.Affiliatedsub-advisors,includingAMIandAMC,willalsoearnadditionalfeesforsub-advisoryservicesrendered.

DuringtheyearendedDecember31,2020,theCompanyrecognizedIMAfeesof$5.3million(2019—$3.5million), ofwhich$2.1million(2019—$2.2million)remainspayabletoAAMEatyearend.

Management Consulting Agreement

Aspreviouslydisclosed,theCompanyenteredintoaManagementConsultingAgreement,datedMarch28,2019(the“ManagementConsultingAgreement”),withAMH.PursuanttotheManagementConsultingAgreement,AMHwillprovideuswithmanagementconsultingandadvisoryservicesrelatedtothebusinessandaffairsoftheCompanyanditssubsidiariesandwewillpaytoAMHinconsiderationforitsservicesundertheManagementConsultingAgreementanannualmanagementconsultingfeeequaltothegreaterof(i)1%oftheconsolidatednetincomeoftheCompanyanditssubsidiariesfortheapplicablefiscalyear,and(ii)$5million.

During the year ended December 31, 2020, the Company recognized Management Consulting fees of $5.0 million (2019 —$4.4 million), of which noneremainspayabletoAMHatyearend(2019—$1.3million).

Other Payables to Related Parties

AsatyearendDecember31,2020,theCompanyhadanintercompanypayablebalanceof$14.4million(2019—$18.1million),duetoitsparent,HighlandsBermudaHoldco,Ltd.

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20. Commitments and Contingent Liabilities

(a) Restricted assetsTheCompany’ssubsidiariesareobligedbythetermsofitscontractualobligationstoU.S.policyholdersandbyobligationstocertainregulatoryauthoritiesto

facilitateissueoflettersofcreditormaintaincertainbalancesintrustfundsforthebenefitofpolicyholders.ThefollowingtabledetailstheformsandvalueofCompany’smaterialrestrictedassetsasatDecember31,2020and2019:

As at December 31, 2020 At December 31, 2019 ($ in millions, except percentages)Regulatorytrustsanddeposits:

Affiliatedtransactions $ 1,027.9 $ 754.9Thirdparty 2,762.2 2,766.6

Lettersofcredit/guarantees 516.8 635.4Totalrestrictedassets(excludingilliquidassets) 4,306.9 4,156.9

Otherinvestments—realestatefund(illiquidassets) 109.4 111.4Totalrestrictedassetsandilliquidassets $ 4,416.3 $ 4,268.3

Totalaspercentofcashandinvestedassets 58.6% 54.4%

AsatDecember31,2020,theCompanyhadpledgedfundsof$516.8million(December31,2019—$635.4million)ascollateralforthesecuredlettersofcredit.Investable assets comprise total investments, cash and cash equivalents, accrued interest, receivables for securities sold and payables for securitiespurchased.

Investments — Equity Method. InMarch2021,thecompanycommittedanadditional$0.8millionequitycontributiontoMVIovera2yearperiod.Real Estate Fund.Investmentsintherealestatefundmayberedeemedonaquarterlybasiswith90days’noticesubjecttoavailablecashinthefundoncethe

lock-up period ends two years after the capital call. If sufficient cash is not available then all requested redemptions will be made on a pro rata basis. If aredemptionrequesthasnotbeenmetinfull,asofsuchcalendarquarter,theremainingportionoftherequestwillberedeemedinsubsequentquarters.TherearenoassurancesastowhentheCompanymaybeabletowithdraw,inwholeorinpart,itsredemptionrequestfromthefund.Alock-upperiodistheinitialamountoftimeaninvestoriscontractuallyrequiredtoremaininvestedbeforehavingtheabilitytoredeem.

OnDecember23,2019,theCompanycommitted$5.0millionasanequityinvestmentintheholdingcompanyofamulti-linereinsurer.Thestrategyforthemulti-linereinsureristocombineadiversifiedreinsurancebusiness,focusedprimarilyonlong-tailedlinesofpropertyandcasualtybusinessand,potentiallytoalesserextent,lifebusiness,withadiversifiedinvestmentstrategy.OnDecember27,2019,theCompanyreceivedademandforaninitialcapitalcallof$0.2millionandpaidthecapitalonJanuary15,2020.Duringthecourseof2020,afurther$0.3millioncapitalwasinvestedinmulti-linereinsurer.

TheCompany’scurrentarrangementswithourbankersfortheissueoflettersofcreditrequireustoprovidecollateralintheformofcashandinvestmentsforthefullamountofallsecuredandundrawnlettersofcreditthatareoutstanding.Wemonitortheproportionofourotherwiseliquidassetsthatarecommittedtotrustfundsortothecollateralizationoflettersofcredit.AsatDecember31,2020and2019,thesefundsamountedtoapproximately58.6%ofthe$7.5billionandapproximately54.4%ofthe$7.8billionofinvestableassetsheldbytheCompany,respectively.Wedonotconsiderthatthisundulyrestrictsourliquidityatthistime.Formoreinformationonourcreditfacilitiesandlong-termdebtarrangements,refertoNote23,“CreditFacilityandLong-termDebt”oftheseconsolidatedfinancialstatements.

Funds at Lloyd’s.AULoperatesatLloyd’sasthecorporatememberforSyndicate4711.Lloyd’sdeterminesSyndicate4711’srequiredregulatorycapitalprincipallythroughthesyndicate’sannualbusinessplan.Suchcapital,calledFundsatLloyd’s,consistsofinvestableassetsasatDecember31,2020intheamountof$541.4million(2019—$513.1million).

TheamountsprovidedasFundsatLloyd’swillbedrawnuponandbecomealiabilityoftheCompanyintheeventofSyndicate4711declaringalossatalevelthatcannotbefundedfromotherresources,orifSyndicate4711requiresfundstocoverashorttermliquiditygap.TheamountwhichtheCompanyprovidesas Funds at Lloyd’s is not available for distribution to the Company for the payment of dividends. Aspen Managing Agency Limited, the managing agent toSyndicate4711,isalsorequiredbyLloyd’stomaintainaminimumlevelofcapitalwhichasatDecember31,2020was£0.4million(December31,2019—£0.4million).ThisisnotavailablefordistributionbytheCompanyforthepaymentofdividends.

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U.S. Reinsurance Trust Fund.For its U.S. reinsurance activities, Aspen U.K. has established and must retain a multi-beneficiary U.S. trust fund for thebenefit ofitsU.S.cedantssothattheymaytakefinancialstatementcredit withouttheneedtopostcedant-specificsecurity.Theminimumtrustfundamountis$20.0 million plus an amount equal to 100%of AspenU.K.’s U.S. reinsurance liabilities, whichwere $1,455.3million as at December 31, 2020and$1,374.4million as at December 31, 2019. As at December 31, 2020, the balance (including applicable letter of credit facilities) held in the trust was $1,478.0 million(2019—$1,395.2million).

AspenBermudahasalsoestablishedandmustretainamulti-beneficiaryU.S.trustfundforthebenefitofitsU.S.cedantssothattheymaytakefinancialstatement credit without the need to post cedant-specific security. The minimumtrust fund amount is $20.0 million plus an amount equal to 100%of AspenBermuda’sliabilitiestoitsU.S.cedantswhichwas$382.8millionand$427.7millionasatDecember31,2020and2019,respectively.AsatDecember31,2020,thebalanceheldintheU.S.trustfundandotherAspenBermudatrustswas$572.3million(2019—$846.2million).

U.S. Surplus Lines Trust Fund.AspenU.K.andSyndicate4711havealsoestablishedaU.S.surpluslinestrustfundwithaU.S.banktosecureliabilitiesunderU.S.surpluslinespolicies.ThebalanceheldintrustasatDecember31,2020was$208.0million(2019—$215.5million).

U.S. Regulatory Deposits.AsatDecember31,2020,AspenSpecialtyhadatotalof$6.7million(2019—$6.1million)ondepositwithsixU.S.statesinordertosatisfystateregulationsforwritingbusinessinthosestates.AAIChadafurther$6.1million(2019—$6.7million)ondepositwithtwelveU.S.states.

Canadian Trust Fund.AspenU.K.hasestablishedaCanadiantrustfundwithaCanadianbanktosecureaCanadianinsurancelicense.AsatDecember31,2020,thebalanceheldintrustwasCAD$156.8million(2019—CAD$155.4million).

Australian Trust Fund.AspenU.K.hasestablishedanAustraliantrustfundwithanAustralianbanktosecurepolicyholderliabilitiesandasaconditionformaintaininganAustralianinsurancelicense.AsatDecember31,2020,thebalanceheldintrustwasAUD$256.6million(2019—AUD$226.9million).

Swiss Trust Fund.AspenU.K.hasestablishedaSwisstrustfundwithaSwissbanktosecurepolicyholderliabilitiesandasaconditionformaintainingaSwissinsurancelicense.AsatDecember31,2020,thebalanceheldintrustwasCHF8.0million(2019—CHF8.4million).

Singapore Fund.AspenU.K.hasestablishedasegregatedSingaporeanbankaccounttosecurepolicyholderliabilitiesandasaconditionformaintainingaSingaporean insurance license and meet local solvency requirements. As at December 31, 2020, the balance in the account was SGD$148.9 million (2019 —SGD$148.9million).(b)Variable interest entities

AsatDecember31,2020,theCompanyhadinvestmentsinone(December31,2019—one)variableinterestentities,PeregrineReinsuranceLtd.

Peregrine Reinsurance Ltd. ForfurtherinformationregardingtheCompany’sinvestmentinPeregrineReinsuranceLtd,refertoNote5,“VariableInterestEntities”oftheseconsolidatedfinancialstatements.

(c) Contingent liabilities Incommonwiththerestoftheinsuranceandreinsuranceindustry,theCompanyisalsosubjecttolitigationandarbitrationintheordinarycourseofbusiness.

TheCompany’sOperatingSubsidiariesareregularlyengagedintheinvestigation,conductanddefenseofdisputes,orpotentialdisputes,resultingfromquestionsofinsuranceorreinsurancecoverageorclaimsactivities.Pursuanttoinsuranceandreinsurancearrangements,manyofthesedisputesareresolvedbyarbitrationorotherformsofalternativedisputeresolution.SuchlegalproceedingsareconsideredinconnectionwithestimatingtheCompany’sInsuranceReserves—LossandLossAdjustmentExpenses,asprovidedontheCompany’sconsolidatedbalancesheet.

Insomejurisdictions,noticeablytheU.S.,afailuretodealwithsuchdisputesorpotentialdisputesinanappropriatemannercouldresultinanawardof“badfaith” punitive damages against the Company’s OperatingSubsidiaries. In accordance with ASC450-20-50-4b, for (a) reasonably possible losses for whichnoaccrualismadebecauseanyoftheconditionsforaccrualinASC450-20-25-2arenotmetand(b)reasonablypossiblelossesinexcessoftheamountsaccruedpursuanttoASC450-20-30-1,theCompanywillprovideanestimateofthepossiblelossorrangeofpossiblelossorstatethatsuchanestimatecannotbemade.

AsatDecember31,2020,itwastheopinionoftheCompany’smanagementbasedonavailableinformationthattheprobabilityoftheultimateresolutionofpendingorthreatenedlitigationorarbitrationshavingamaterialeffectontheCompany’sfinancialcondition,resultsofoperationsorliquiditywouldberemote.

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21.Concentrations of Credit RiskThe Company is potentially exposed to concentrations of credit risk in respect of amounts recoverable from reinsurers, investments and cash and cash

equivalents,andinsuranceandreinsurancebalancesowedbythebrokerswithwhomtheCompanytransactsbusiness.

TheCompanydefinescredit risktolerancesinlinewiththeriskappetitesetbyourBoardandthey,togetherwiththegroup’sriskmanagementfunction,monitorexposurestoindividualcounterparties.AnyexceptionsarereportedtoseniormanagementandtheRiskCommitteeoftheBoardofDirectors.

Reinsurance recoverablesThetotalamountrecoverablebytheCompanyfromreinsurersasatDecember31,2020was$3,195.2million(2019—$2,319.8million)ofwhich$2,010

millionwasuncollateralized(2019—$1,817.5million).AsatDecember31,2020,oftheCompany’suncollateralizedreinsurancerecoverables11.0%(2019—15.1%)werewithMunichRewhichisratedA+byA.M.BestandAA-byS&P,13.4%(2019—11.9%)werewithEverestRewhichisratedA+byA.MBestandA+byS&P,and9.2%(2019—8.9%)werewithLloyd’swhichisratedAbyA.M.BestandA+byS&P.ThesearetheCompany’slargestexposurestoindividualreinsurers.

OnJune16,2016,theFASBissuedASU2016-13,“Financial Instruments - Credit Losses (Topic 326)”whichintroducedanewimpairmentmodel,knownasthecurrentexpectedlossmodel(“CECL”),whichisbasedonexpectedlossesratherthanincurredlosses.Underthenewcreditlossmodel,theCompanywouldrecognizeanallowanceforitsestimateofexpectedcreditlossesandthiswouldapplytoreinsurancereceivables.FollowingtheadoptionofthisASUwitheffectfrom January 1, 2020, the Company recognized a reduction in the Company’s reinsurance recoverables by $3.7 million. For the twelve months endedDecember31,2020therewasanincreaseintheCECLallowanceonreinsurancerecoverablesof$0.1million.

Underwriting premium receivablesThetotalunderwritingpremiumreceivablebytheCompanyasatDecember31,2020was$1,279.8million(2019—$1,318.4million).AsatDecember31,

2020, $11.4 million of the total underwriting premium receivable balance has been due for settlement for more than one year. The Company assesses therecoverabilityofpremiumreceivablesthroughareviewofpoliciesandtheconcentrationofreceivablesbybroker.Allowanceforcreditlossesof$34.0millionasatDecember31,2020(2019—$23.0million)forunderwritingpremiumsunlikelytobecollected.

Investments and cash and cash equivalentsTheCompany’sinvestmentpoliciesincludespecificprovisionsthatlimittheallowableholdingsofasingleissueandissuer.AsatDecember31,2020,there

were no investments in any single issuer, other than the U.S. government, U.S. government agencies, U.S. government sponsored enterprises, the CanadiangovernmentandtheU.K.governmentinexcessof2%oftheaggregateinvestmentportfolio.Balances owed by brokers

TheCompanyunderwritesasignificantamountofitsbusinessthroughbrokersandacreditriskexistsshouldanyofthesebrokersbeunabletofulfilltheircontractual obligations in respect of insurance or reinsurance balances due to the Company. The following table shows the largest brokers that the CompanytransactedbusinesswithinthethreeyearsendedDecember31,2020andtheproportionofgrosswrittenpremiumsfromeachofthosebrokers. Twelve Months Ended December 31, 2020 2019 2018

(in percentages)AonCorporation 15.8% 13.4% 15.8%Marsh&McLennanCompanies,Inc. 15.4 13.6 15.8WillisGroupHoldings,Ltd. 10.4 10.3 12.4Otherbrokers/non-brokersources 58.4 62.7 56.0

Total 100.0% 100.0% 100.0%

Grosswrittenpremiums($millions) $ 3,703.6 $ 3,442.4 $ 3,446.9

______________OnMarch9,2020,AonplcandWillisTowersWatsonannouncedadefinitiveagreementtocombine,andexpectthetransactiontocloseinthefirsthalfof2021.

Nootherindividualbrokeraccountedformorethan10%oftotalgrosswrittenpremiums.

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22. Reclassifications from Accumulated Other Comprehensive Income

ThefollowingtablesetsoutthecomponentsoftheCompany’sAOCIthatarereclassifiedintotheauditedcondensedconsolidatedstatementofoperationsforthetwelvemonthsendedDecember31,2020and2019:

Amount Reclassified from AOCI

Details about the AOCI ComponentsTwelve Months Ended

December 31, 2020Twelve Months Ended

December 31, 2019Affected Line Item in the

Consolidated Statement of Operations ($ in millions) Availableforsalesecurities:Realized(losses)onsaleofsecurities $ (69.3) $ (14.4) RealizedandunrealizedinvestmentgainsRealizedgainsonsaleofsecurities 2.2 7.6 Realizedandunrealizedinvestmentlosses

(67.1) (6.8) (Loss)fromoperationsbeforeincometaxTaxonnetrealizedgainsofsecurities — — Incometax(expense)/benefit

$ (67.1) $ (6.8) Net(loss)Realizedderivatives:Netrealizedgainsonsettledderivatives 0.3 4.8 General,administrativeandcorporateexpenses

Taxonsettledderivatives — (0.8) Incometax(expense)/benefit$ 0.3 $ 4.0 Net(loss)

TotalreclassificationsfromAOCItothestatementofoperations,netofincometax $ (66.8) $ (2.8) Net(loss)

23.Credit Facility and Long-term DebtInthenormalcourseofitsoperations,theCompanyentersintoagreementswithfinancialinstitutionstoobtainsecuredandunsecuredcreditfacilities.Credit Agreement. OnMarch27,2017,AspenHoldingsandcertainofitsdirectorindirectsubsidiaries(collectively,the“Borrowers”)enteredintoaSecond

Amended and Restated Credit Agreement (the “Credit Agreement”) with various lenders and Barclays Bank plc, as administrative agent, which amends andrestatestheAmendedandRestatedCreditAgreement,datedasofJune12,2013,amongtheCompany,certainsubsidiariesthereof,variouslendersandBarclaysBankplc,asadministrativeagent.ThecreditfacilitywillbeusedbytheBorrowerstofinancetheworkingcapitalneedsoftheCompanyanditssubsidiaries,forlettersofcreditinconnectionwiththeinsuranceandreinsurancebusinessesoftheCompanyanditssubsidiariesandforothergeneralcorporatepurposes.Initialavailabilityunderthecreditfacilityis$200,000,000andtheCompanyhastheoption(subjecttoobtainingcommitmentsfromacceptablelenders)toincreasethecreditfacilitybyupto$100,000,000.ThecreditfacilitywillexpireonMarch27,2022.

AsatDecember31,2020,noborrowingswereoutstandingundertheCreditAgreement.Thefeesandinterestratesontheloansandthefeesonthelettersofcredit payablebytheBorrowersundertheCreditAgreementarebaseduponthecredit ratingsfortheCompany’slong-termunsecuredseniordebtbyS&PandMoody’s.Inaddition,thefeesforaletterofcreditvarybaseduponwhethertheapplicableBorrowerhasprovidedcollateral(intheformofcashorqualifyingdebtsecurities)tosecureitsreimbursementobligationswithrespecttosuchletterofcredit.

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UndertheCreditAgreement,theCompanymustnotpermit(a)consolidatedtangiblenetworthtobelessthanapproximately$1,891,000,000plus25%ofconsolidatednetincomeand25%ofaggregatenetcashproceedsfromtheissuancebytheCompanyofitscapitalstock,ineachcaseafterJanuary1,2020,(b)theratioofitstotalconsolidateddebttothesumofsuchdebtplusourconsolidatedtangiblenetworthtoexceed35%or(c)anymaterialinsurancesubsidiarytohaveafinancial strength rating of less than “B++” from A.M. Best. The Credit Agreement contains other customary affirmative and negative covenants, including(subjecttovariousexceptions)restrictionsontheabilityoftheCompanyanditssubsidiariestoincurindebtedness,createorpermitliensontheirassets,engageinmergersorconsolidations,disposeofassets,paydividendsorotherdistributions,purchaseorredeemtheCompany’sequitysecurities,makeinvestmentsandenterintotransactionswithaffiliates.Inaddition,theCreditAgreementhascustomaryeventsofdefault,including(subjecttocertainmaterialitythresholdsandgraceperiods)paymentdefault, failuretocomplywithcovenants,materialinaccuracyofrepresentationorwarranty,bankruptcyorinsolvencyproceedings,changeofcontrolandcross-defaulttootherdebtagreements.

Other Credit Facilities.(i)OnSeptember20,2019,AspenBermudaandCitibankEuropeplc(“CitiEurope”)amendedthecommittedletterofcreditfacility,datedJune30,2012,

asamendedonJune30,2014,June30,2016,June29,2018andJune30,2020(the“LOCFacility”).ThelatestamendmenttotheLOCFacilityextendsthetermtoJune30, 2022. Themaximumaggregate amount available under the LOCFacility is $500.0million. Under the LOCFacility, AspenBermudawill payto CitiEurope(a)aletterofcreditfeebasedontheavailableamountsofeachletterofcreditand(b)acommitmentfee,whichvariesbaseduponusage,ontheunutilizedportionoftheLOCFacility.AspenBermudawillalsopayinterestontheamountdrawnbyanybeneficiaryundertheLOCFacilityatarateperannumofLIBORplus 1% (plus reserve asset costs, if any) fromthe date of drawinguntil the date of reimbursement byAspenBermuda. In addition, AspenBermudaandCitiEuropeenteredintoanuncommittedletterofcreditfacilitywherebyAspenBermudahastheabilitytorequestlettersofcreditunderthisfacilitysubjecttothepriorapproval ofCiti Europe. Thefeeassociatedwiththeuncommittedfacility is aletter ofcredit feebasedontheavailableamountsofeachletter ofcredit issuedunder the uncommitted facility. Both the LOCFacility and the uncommitted facility are used to secure obligations of Aspen Bermuda to its policyholders. Inadditiontothesefacilities,wealsouseregulatorytruststosecureourobligationstopolicyholders.

ThetermsofapledgeagreementbetweenAspenBermudaandCitiEurope(pursuanttoanassignmentagreementdatedOctober11,2006)datedJanuary17,2006, as amended, were also amended on June 30, 2014to change the types of securities or other assets that are acceptable as collateral under the NewLOCFacility.AllotheragreementsrelatingtoAspenBermuda’sLOCFacility,whichnowapplytotheLOCFacilitywithCitiEurope,aspreviouslyfiledwiththeSEC,remain in full force and effect. As at December 31, 2020, we had $444.2 million of outstanding collateralized letters of credit under the LOC Facility(December31,2019—$444.2million).

(ii)OnFebruary11,2019,AspenEuropeanandAspenHoldings(actingasguarantorofAspenEuropean)enteredintoaletterofcreditfacilityforthepurposeofobtainingaletterofcreditinfavorofAspenU.K.forasumnottoexceed$100milliontoprovideapprovedregulatorycapitalforAspenU.K.AletterofcreditwasissuedinfavorofAspenU.K.forasumof$100millionwhichexpiresonFebruary11,2023.

(iii)OnNovember3,2020,AULandAspenHoldings(actingasguarantorofAUL)enteredintoaletterofcreditfacilityfortheaccountofAULtosupportAUL’sFundsatLloyd’srequirements.Thisfacilityterminatesfouryearsfromthedateofnoticefromthelendertothebeneficiaryoftheletterofcredit,andprovidesamaximumaggregateamountofupto$40million.AletterofcreditwasissuedinfavorofLloyd’sforasumof$40million.

(iv)OnNovember25,2020,AULandAspenHoldings(actingasguarantorofAUL)enteredintoaFundsatLloyd’sFacilityAgreementfortheaccountofAULpursuanttowhichthelenderprovidescollateralforthebenefitofLloyd’stosupportAUL’sFundsatLloyd’srequirements.ThisfacilityterminatesonDecember31,2021,unlessextendedtoDecember31,2022pursuanttothetermsofthefacilityagreement,andprovidesthatamaximumaggregateamountofupto$80millionmaybedepositedwithLloyd’sonbehalfofAUL.AsatDecember31,2020,aFALdepositof$80millionwasmadeonbehalfofAULunderthisfacility.

(v)OnNovember30,2020,AULandAspenBermuda(actingasAUL’sguarantor)enteredintoaFundsatLloyd’sFacilityAgreement,fortheaccountofAUL,pursuanttowhichthelenderpledgessecuritiesforthebenefitofLloyd’stosupportAUL’sFundsatLloyd’srequirements.Thisfacilityisforaoneyear,subjecttoannualautomaticextensions,andprovidesthatamaximumaggregateamountofupto$100millionmaybepledgedonbehalfofAUL.AsatDecember31,2020,$100millioninsecuritieswerepledgedonbehalfofAULunderthisfacility.

Theabovecreditfacilitiesincludecertainrestrictivecovenantscustomaryforfacilitiesofthistype,includingrestrictionsonindebtedness,consolidatedtangiblenetworth,andminimumfinancialstrengthratings.Inaddition,theagreementsinclude

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defaultcovenants,whichcouldrequiretheCompanytofullysecuretheoutstandingamountsthereunderand/orresultintheCompanynotbeingallowedtoissueanynewlettersofcredit.

Long-term Debt.OnDecember15,2010,theCompanycloseditsofferingof$250.0million6.00%SeniorNotesdueDecember15,2020.Thenetproceedsfromthisoffering,beforeofferingexpenses,were$247.5million.OnJune18,2018,weredeemed$125.0millionofour6.00%SeniorNotesdue2020resultinginarealizedloss,ormake-wholepayment,of$8.6million.OnSeptember30,2019,weredeemedtheremaining$125.0millionofour6.00%SeniorNotesdue2020resultinginarealizedloss,ormake-wholepaymentof$5.5million.

OnNovember13,2013,theCompanycloseditsofferingof$300.0million4.65%SeniorNotesdueNovember15,2023(the“2023SeniorNotes”).Thenetproceeds from the 2023 Senior Notes offering, before offering expenses, were $299.7 million and a portion of the proceeds was used to redeem the thenoutstanding2014SeniorNotes.Subjecttoapplicablelaw,the2023SeniorNoteswillbetheseniorunsecuredobligationsofAspenHoldingsandwillrankequallyinrightofpaymentwithallofourotherseniorunsecuredindebtednessfromtimetotimeoutstanding.

Subjecttocertainexceptions,solongasanyoftheseniornotesdescribedaboveremainoutstanding,theCompanyhasagreedthatneithertheCompanynoranyofitssubsidiarieswill(i)createalienonanysharesofcapitalstockofanydesignatedsubsidiary(currentlyAspenU.K.andAspenBermuda,asdefinedintheIndenture),or(ii)issue,sell,assign,transferorotherwisedisposeofanysharesofcapitalstockofanydesignatedsubsidiary.CertaineventswillconstituteaneventofdefaultundertheIndenture,includingdefaultinpaymentatmaturityofanyofourotherindebtednessinexcessof$50.0million.

Thefollowingtablesummarizesourcontractualobligationsunderlong-termdebtasatDecember31,2020. Payments Due By Period

Contractual BasisLess than

1 year 1-3 years 3-5 years More than 5

years Total ($ in millions)Long-termDebtObligations $ — $ 300.0 $ — $ — $ 300.0

TheSeniorNotesobligationdisclosedabovedoesnotincludethe$14.0millionannualinterestpayableassociatedwiththeSeniorNotesortheloannotesissuedbySilverton.FormoreinformationonSilverton,refertoNote5,“VariableInterestEntities”oftheseconsolidatedfinancialstatements.

24. Allowance for Expected Credit Losses

ThefollowingtablesummarizestheCompany’sallowanceforexpectedcreditlossesforthetwelvemonthsendedDecember31,2020ininvestments,reinsurancerecoverablesandreceivablesfollowingtheadoptionofASU2016-13Financial Instruments - Credit Losses (Topic 326)”:

Twelve Months Ended December 31, 2020($ in millions)

Investments Reinsurance Recoverables Receivables

OpeningvalueasatJanuary1,2020 $ 0.6 $ 3.7 $ 23.0Movementoftheallowanceforcreditlossesduringtheyear (0.4) 0.1 11.0ClosingvalueasatDecember31,2020 $ 0.2 $ 3.8 $ 34.0

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25. Subsequent Events

Insurance sub-segment: changes to principal lines of business. DuetothechangeinmanagementstructurewitheffectfromJanuary1,2021,theCompany’sInsurancesegmentsprincipallinesofbusinesshavechanged,asshowninthefollowingtable:

Insurance SegmentCurrentsub-segment:principallinesofbusiness Newsub-segment:principallinesofbusiness

Propertyandcasualtyinsurance FirstpartyandspecialtyinsuranceMarine,aviationandenergyinsurance CasualtyandliabilityinsuranceFinancialandprofessionallinesinsurance Financialandprofessionallinesinsurance

Ouroperatingandreportingsegments,InsuranceandReinsuranceremainunchanged.ThechangewillbelimitedtotheprincipallinesofbusinesswithinourInsurancesegment.

Weanticipate, for our interimandannual financial reporting for the year-ended December 31, 2021, the following comparative financial metrics will berepresentedtocomplywiththenewInsurancesub-segmentprincipal lineofbusinessstructure: (i) grossandnet writtenpremiumsbylineofbusiness; (ii) lossdevelopmenttriangles;(iii)Item4B,“BusinessSegments”;and(iv)Item5,“OperatingandFinancialReviewandProspects”.

Federal Home Loan Bank of Boston. TheCompany’s subsidiaries, AAICandAspenSpecialty, eachestablishedasecuredlineof credit at Federal HomeLoanBankofBoston(“FHLBB”)onApril1,2021.Advancesmaybeusedtosupportgeneralcorporatepurposes.Themaximumamountavailableunderthesefacilitieswillvarybasedontheborrower’snetadmittedassetsandthelender’sunderwritingcriteria.AspenSpecialty’smaximumborrowingcapacityavailablefromtheFHLBBisapproximately$98million.UnderTexasstateinsurancelaw,withoutthepriorconsentoftheTexasDepartmentofInsurance,theamountofassetsAAICmaypledgetosecuredebtobligationsislimitedto10%ofitsreserveassets,resultinginamaximumborrowingcapacityforAAICunderitsFHLBBfacilityofapproximately$97million.NeitherAAICnorAspenSpecialtyexpectstodrawonthesefacilitiesinthenearfuture.

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REPORT OF THE INDEPENDENT REGISTERED PUBLIC ACCOUNTING FIRM

TotheBoardofDirectorsandShareholdersofAspenInsuranceHoldingsLimited

Opinion on the Consolidated Financial Statements

WehaveauditedtheaccompanyingconsolidatedbalancesheetsofAspenInsuranceHoldingsLimitedandsubsidiaries(the“Company”)asofDecember31,2020and2019,therelatedconsolidatedstatementsofoperationsandothercomprehensiveincome,changesinshareholders’equity,andcashflowsforeachoftheyearsinthethree‑yearperiodendedDecember31,2020,andtherelatednotesandfinancialstatementschedulesItoV(collectively,theconsolidatedfinancialstatements).Inouropinion,theconsolidatedfinancialstatementspresentfairly,inallmaterialrespects,thefinancialpositionoftheCompanyasofDecember31,2020and2019,andtheresultsofitsoperationsanditscashflowsforeachoftheyearsinthethree‑yearperiodendedDecember31,2020,inconformitywithU.S.generallyacceptedaccountingprinciples.

Basis for Opinion

TheseconsolidatedfinancialstatementsaretheresponsibilityoftheCompany’smanagement.Ourresponsibilityistoexpressanopinionontheseconsolidatedfinancialstatementsbasedonouraudits.WeareapublicaccountingfirmregisteredwiththePublicCompanyAccountingOversightBoard(UnitedStates)(PCAOB)andarerequiredtobeindependentwithrespecttotheCompanyinaccordancewiththeU.S.federalsecuritieslawsandtheapplicablerulesandregulationsoftheSecuritiesandExchangeCommissionandthePCAOB.

WeconductedourauditsinaccordancewiththestandardsofthePCAOB.Thosestandardsrequirethatweplanandperformtheaudittoobtainreasonableassuranceaboutwhethertheconsolidatedfinancialstatementsarefreeofmaterialmisstatement,whetherduetoerrororfraud.TheCompanyisnotrequiredtohave,norwereweengagedtoperform,anauditofitsinternalcontroloverfinancialreporting.Aspartofouraudits,wearerequiredtoobtainanunderstandingofinternalcontroloverfinancialreportingbutnotforthepurposeofexpressinganopinionontheeffectivenessoftheCompany’sinternalcontroloverfinancialreporting.Accordingly,weexpressnosuchopinion.

Ourauditsincludedperformingprocedurestoassesstherisksofmaterialmisstatementoftheconsolidatedfinancialstatements,whetherduetoerrororfraud,andperformingproceduresthatrespondtothoserisks.Suchproceduresincludedexamining,onatestbasis,evidenceregardingtheamountsanddisclosuresintheconsolidatedfinancialstatements.Ourauditsalsoincludedevaluatingtheaccountingprinciplesusedandsignificantestimatesmadebymanagement,aswellasevaluatingtheoverallpresentationoftheconsolidatedfinancialstatements.Webelievethatourauditsprovideareasonablebasisforouropinion.

Critical Audit Matters

Thecriticalauditmatterscommunicatedbelowaremattersarisingfromthecurrentperiodauditoftheconsolidatedfinancialstatementsthatwerecommunicatedorrequiredtobecommunicatedtotheauditcommitteeandthat:(1)relatetoaccountsordisclosuresthatarematerialtotheconsolidatedfinancialstatementsand(2)involvedourespeciallychallenging,subjective,orcomplexjudgments.Thecommunicationofcriticalauditmattersdoesnotalterinanywayouropinionontheconsolidatedfinancial statements, takenas a whole, andweare not, bycommunicating the critical audit matters below, providingseparate opinionsonthecriticalauditmattersorontheaccountsordisclosurestowhichtheyrelate.

Estimate of claims Incurred but not reported

As discussed in Note 2(b) and Note 10 to the consolidated financial statements, the liability for unpaid losses and loss adjustment expense (LAE) representsreservesestablishedforthetotalunpaidcostofclaimsinrespectofeventsthathaveoccurredbythebalancesheetdate,includingtheCompany’sestimatesofthetotalcostofclaimsincurredbutnotyetreported(“IBNR”).AsofDecember31,2020,theCompany’stotalliabilityforunpaidlossesandlossadjustmentexpensesincludingIBNRis$7,165.3million.

WeidentifiedtheestimateofIBNRincludedinunpaidlossesandLAEasacriticalauditmatter.SpecializedskillsandknowledgewererequiredtoassesstheactuarialmethodologiesandassumptionsusedtoestimatetheIBNRincludedinunpaidlossesandLAE,includinglossratiosonthemostrecentaccidentyearsandlossdevelopmentpatterns.

Thefollowingaretheprimaryproceduresweperformedtoaddressthiscriticalauditmatter.

WeevaluatedthedesignandimplementationandtestedtheoperatingeffectivenessofaninternalcontrolrelatedtotheCompany’sprocesstoestimateIBNR,specificallyrelatingtothereservingmethodologiesandassumptionsapplied.

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Wealsoinvolvedactuarialprofessionalswithspecializedskillandknowledgewhoassistedin:

• developing an independent estimate of reserves, including IBNR, for selected lines of business using the Company’s actual historical data and lossdevelopmentpatterns,aswellasindustrydataandotherbenchmarks,andcomparingtomanagement’sactuariallydeterminedreserveestimates

• evaluating management’s actuarial reserving methodologies andactuarial assumptions impacting unpaid losses andloss adjustment expenses, includingIBNR,andtheconsistencyofmanagement’sapproachperiod-over-periodbycomparingthemtogenerallyacceptedactuarialmethods

•evaluatingtheCompany’shistoricalabilitytoestimateunpaidlossesbycomparingtheprogressionofclaimspaidagainsttheestimatedliabilityforunpaidlosses.

Fair value of privately-held investments

AsdiscussedinNotes2(c)and6totheconsolidatedfinancialstatements,theCompanyhasestablishedpoliciesandproceduresfordeterminingthefairvalueofprivately-heldinvestments.AsofDecember31,2020,therecordedbalancesoftheCompany’sprivately-heldinvestmentsclassifiedasLevel3inthefairvaluehierarchywere$299.3million.TheCompany’sprivately-heldinvestmentsprimarilycomprisecommercialmortgageloansandmiddle-marketloans.

Weidentifiedtheassessmentoffairvalueofprivately-heldinvestmentsasacriticalauditmatter.Duetothesignificantmeasurementuncertaintyassociatedwiththefairvalueofsuchinvestments,subjectiveauditorjudgementwasrequiredtoevaluatethemodels’significantinputsandassumptionswhichwerenotdirectlyobservableinfinancialmarkets,suchasthediscountrateandthetimingandamountofcashflows.Therewasalsoahighdegreeofsubjectivityandauditorjudgementinevaluatingthemethodologyusedtodevelopthediscountedcashflowmodels.Thefollowingaretheprimaryproceduresweperformedtoaddressthiscriticalauditmatter:

WeevaluatedtheCompany’smethodologyanditsabilitytoproduceafairvalueestimateinaccordancewithFinancialAccountingStandardsBoardTopicASC820,FairValueMeasurement,forprivately-heldinvestments.Weinvolvedfinancialinstrumentvaluationprofessionalswithspecializedskillsandknowledge,whoassistedindevelopinganindependentestimateoffairvalueforcertaininvestmentsusingmarketdatasourcesandcomparingittotheCompany’svalue.

Estimate of reinsurance recoverables on claims incurred but not reported

As discussed in Note 2(b) and Note 7 to the consolidated financial statements, the estimated amounts recoverable from reinsurers on unpaid losses and lossadjustment expenses are reflected as assets in the financial statements. As of December 31, 2020, the Company’s total reinsurance recoverables includingreinsurancerecoverablesonclaimsincurredbutnotreported(“CededIBNR”)were$3,195.2million.

WeidentifiedtheestimateofreinsurancerecoverablesonCededIBNRasacriticalauditmatter.Subjectiveandcomplexauditorjudgement,includingspecializedskillsandknowledge,wasinvolvedinevaluating(1)theassumptionsusedfornetreserving,includingnetandgrosslossratios,acrossunderwritingyearsandlinesofbusiness,and(2)theassumptions,includinglossdistribution,run-offpatternsandinvestmentreturnappliedtoperformtherisktransfertestonasignificantreinsurancecontractenteredintoduringtheperiod.

Thefollowingaretheprimaryproceduresweperformedtoaddressthiscriticalauditmatter.

WeevaluatedthedesignandtestedtheoperatingeffectivenessofcertaininternalcontrolsrelatedtotheestimateofreinsurancerecoverablesonCededIBNR.Thisincludedcontrolsrelatedtothereviewofnetreservingassumptionsappliedandtherisktransfertest.

Weinvolvedactuarialprofessionalswithspecializedskillandknowledgewhoassistedin:

• assessing the Company’s ratio of net loss and loss adjustment expenses to gross loss and loss adjustment expenses and net earned premiumto grossearnedpremium,alongwithchangesintheseratiossinceDecember31,2019forthere-projectedclassesbycomparingthemtothoseexpectedfromtheCompany’soutwardsreinsuranceprogramme

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• assessingtheCompany’sratioofnetlossandlossadjustmentexpensestogrosslossandlossadjustmentexpensesbycomparingagainsttheCompany’sratioofnetearnedpremiumtogrossearnedpremiumbyclassofbusiness

• performingsensitivityanalysisovertheassumptionsusedintherisktransfertesttoassesstheimpactofchangesinthoseassumptionsontheresultoftherisktransfertest

• evaluatingassumptionsusedintherisktransfer test, includinglossdistribution, run-off patternsandinvestment returnusedintherisktransfer test byassessingthesourceoftheassumptionsused.

/s/KPMGLLPKPMGLLP

WehaveservedastheCompany’sauditorsince2002.

London,UnitedKingdomApril9,2021

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INDEX OF FINANCIAL STATEMENT SCHEDULES Page ScheduleI—Investments 1ScheduleII—CondensedFinancialInformationofRegistrant 2ScheduleIII—SupplementaryInsuranceInformation 5ScheduleIV—Reinsurance 6ScheduleV—ValuationandQualifyingAccounts 7

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ASPEN INSURANCE HOLDINGS LIMITED

SCHEDULE I - INVESTMENTSFor the Twelve Months Ended December 31, 2020, 2019 and 2018

TheCompany’sinvestmentscompriseinvestmentsinsubsidiaries.

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ASPEN INSURANCE HOLDINGS LIMITEDSCHEDULE II - CONDENSED FINANCIAL INFORMATION OF REGISTRANT

BALANCE SHEETSAs at December 31, 2020 and 2019

As at December 31, 2020 As at December 31, 2019 ($ in millions, except per share amounts)ASSETS Fixedincomematurities(trading) — 75.6Cashandcashequivalents 92.4 37.4Investmentsinsubsidiaries 3,325.6 2,973.6Intercompanyfundsduefromaffiliates 0.7 0.1Right-of-useoperatingleaseassets 1.0 1.4Otherassets 6.4 6.9Totalassets $ 3,426.1 $ 3,095.0

LIABILITIES Accruedexpensesandotherpayables 24.3 7.2Intercompanyfundsduetoaffiliates 103.4 61.2Long-termdebt 299.9 299.8Operatingleaseliabilities 0.9 1.3Totalliabilities $ 428.5 $ 369.5

SHAREHOLDERS’EQUITY OrdinaryShares:60,395,839sharesofparvalue$0.01each(December31,2019—60,395,839) $ 0.6 $ 0.6

PreferenceShares:11,000,0005.950%sharesofparvalue0.15144558¢each(December31,2019—11,000,000) — —10,000,0005.625%sharesofparvalue0.15144558¢each(December31,2019—10,000,000) — —10,000,0005.625%depositarysharesofparvalue0.15144558¢each(December31,2019—10,000,000) — —

Additionalpaidincapital 1,469.7 1,201.7Retainedearnings 1,425.7 1,514.6Accumulatedothercomprehensiveincome,netoftaxes: Unrealizedgainsoninvestments 186.8 84.5Gain/(loss)onderivatives 4.6 4.3Gainsonforeigncurrencytranslation (89.8) (80.2)Totalaccumulatedothercomprehensiveincome 101.6 8.6Totalshareholders’equity 2,997.6 2,725.5Totalliabilitiesandshareholders’equity $ 3,426.1 $ 3,095.0

____________________TheCompany’sinvestmentinsubsidiariesareaccountedforundertheequitymethodandadjustmentstothecarryingvalueoftheseinvestmentsaremadebasedontheCompany’sshareof

capital,includingshareofincomeandexpenses.Changesinthevaluewererecognizedinrealizedandunrealizedinvestmentgainsandlossesinthestatementofoperations.

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ASPEN INSURANCE HOLDINGS LIMITEDSCHEDULE II - CONDENSED FINANCIAL INFORMATION OF REGISTRANT - Continued

STATEMENTS OF OPERATIONS AND COMPREHENSIVE INCOME

For the Twelve Months Ended December 31, 2020, 2019 and 2018

Twelve Months EndedDecember 31, 2020

Twelve MonthsEnded December 31,

2019Twelve Months Ended

December 31, 2018 ($ in millions)Operating Activities:

Equityinnetearningsofsubsidiariesandotherinvestments,equitymethod $ (92.1) $ (415.1) $ (371.3)Dividendincome 141.5 270.0 340.3Netrealizedandunrealizedinvestmentgains/(losses) 2.5 2.6 (5.1)Totalrevenues 51.9 (142.5) (36.1)

Expenses:

General,administrativeandcorporateexpenses (74.6) (70.2) (83.8)Interestexpense (14.3) (25.7) (25.9)Otherexpense (3.1) (3.3) —(Loss)fromoperationsbeforeincometax (40.1) (241.7) (145.8)Incometax — — —Net(loss) (40.1) (241.7) (145.8)

Amountattributabletonon-controllinginterest — 1.2 (1.0)Net (loss) attributable to Aspen Insurance Holdings Limited ordinary shareholders (40.1) (240.5) (146.8)Other comprehensive Income/(loss), net of taxes:

Changeinunrealizedgainsoninvestments 102.3 151.3 (76.5)Netchangefromcurrentperiodhedgedtransactions 0.3 4.0 (1.8)Changeinforeigncurrencytranslationadjustment (9.6) (24.8) 12.3Othercomprehensiveincome/(loss),netoftax 93.0 130.5 (66.0)

Comprehensive Income / (loss) $ 52.9 $ (110.0) $ (212.8)

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ASPEN INSURANCE HOLDINGS LIMITEDSCHEDULE II - CONDENSED FINANCIAL INFORMATION OF REGISTRANT - Continued

STATEMENTS OF CASH FLOWS

For the Twelve Months Ended December 31, 2020, 2019 and 2018

Twelve Months EndedDecember 31, 2020

Twelve Months EndedDecember 31, 2019

Twelve Months EndedDecember 31, 2018

($ in millions)

Cash Flows From/(Used In) Operating Activities:

Netincome (excludingequityinnetearningsofsubsidiaries) $ 52.0 $ 174.6 $ 224.5Adjustments:

Share-basedcompensationexpenses — — 10.1Realizedandunrealizedlosses/(gains) 1.5 9.6 (0.7)Lossonderivativecontracts (0.3) (4.0) 1.8Amortizationofright-to-useoperatingleaseassets 0.4 0.3 —Interestonoperatingleaseliabilities (0.4) 0.2 —Changeinotherassets 0.5 2.1 (0.2)Changeinaccruedexpensesandotherpayables 15.9 (51.2) 51.1Changeinintercompanyactivities 41.6 (59.0) 63.9Changeinoperatingleaseliabilities — (0.5) —Netcashgeneratedbyoperatingactivities 111.2 72.1 350.5

Cash Flows From/(Used in) Investing Activities:

Proceeds/(purchases)offixedincomesecurities 75.6 (75.6) 79.4Investmentinsubsidiaries (87.3) (82.7) (215.9)RepaymentofloannotesissuedbySilverton — — 18.6Netcash(usedin)investingactivities (11.7) (158.3) (117.9)

Cash Flows From/(Used in) Financing Activities:

Proceedsfromissuanceofordinaryshares,netofissuancecosts — 1.4 2.7Proceedsfromissuanceofpreferenceshares,netofissuancecosts — 241.6 —Ordinarysharerepurchase — (0.1) —Ordinaryandpreferencesharedividendspaid (44.5) (35.9) (73.4)Repaymentoflong-termdebtissuedbySilverton — (7.7) —Make-wholepayment — (5.5) (8.6)Minorityinterestbuy-out — (0.8) —Long-termdebtredeemed — (125.0) (125.0)Cashpaidfortaxwithholdingpurposes — — (4.7)Netcash(usedin)/fromfinancingactivities (44.5) 68.0 (209.0)Increase/(decrease)incashandcashequivalents 55.0 (18.2) 23.6Cashandcashequivalents—beginningofperiod 37.4 55.6 32.0Cashandcashequivalents—endofperiod $ 92.4 $ 37.4 $ 55.6

_________Netincomehasbeenadjustedfortheproportionduetonon-controllinginterest.

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ASPEN INSURANCE HOLDINGS LIMITEDSCHEDULE III - SUPPLEMENTARY INSURANCE INFORMATION

For the Twelve Months Ended December 31, 2020, 2019 and 2018

Supplementary Information ($ in millions)

Year Ended December 31,2020

DeferredPolicy

AcquisitionCosts

NetReserves

for Lossesand LAE

Net Reserves

for Unearned Premiums

NetPremiums

Earned

NetInvestment

Income

Losses andLAE

Expenses

PolicyAcquisitionExpenses

NetPremiumWritten

Generaland

AdministrativeExpenses

Reinsurance $ 206.8 $ 2,095.7 $ 617.6 $ 1,292.1 $ 958.6 $ 246.0 $ 1,302.1 $ 110.8Insurance 99.8 1,874.4 746.1 1,240.5 882.2 219.7 1,280.8 197.2

Total $ 306.6 $ 3,970.1 $ 1,363.7 $ 2,532.6 $ 154.6 $ 1,840.8 $ 465.7 $ 2,582.9 $ 308.0

Year to date December31, 2019

DeferredPolicy

AcquisitionCosts

NetReserves

for Lossesand LAE

Net Reserves

for Unearned Premiums

Net Premiums

Earned

NetInvestment

Income

Losses andLAE

Expenses

PolicyAcquisitionExpenses

NetPremiumWritten

Generaland

AdministrativeExpenses

Reinsurance $ 210.3 $ 2,605.9 $ 599.9 $ 1,255.2 $ 917.9 $ 264.9 $ 1,251.1 $ 111.7Insurance 80.8 2,026.1 694.1 1,038.1 761.8 147.8 1,176.8 229.8

Total $ 291.1 $ 4,632.0 $ 1,294.0 $ 2,293.3 $ 197.3 $ 1,679.7 $ 412.7 $ 2,427.9 $ 341.5

Year to date December31, 2018

DeferredPolicy

AcquisitionCosts

NetReserves

for Lossesand LAE

Net Reserves

for Unearned Premiums

NetPremiums

Earned

NetInvestment

Income

Losses andLAE

Expenses

PolicyAcquisitionExpenses

NetPremiumWritten

Generaland

AdministrativeExpenses

Reinsurance $ 208.3 $ 2,843.6 $ 616.0 $ 1,256.4 $ 927.0 $ 260.9 $ 1,182.9 $ 118.5Insurance 40.2 2,153.0 534.3 958.3 646.0 110.7 899.1 239.2

Total $ 248.5 $ 4,996.6 $ 1,150.3 $ 2,214.7 $ 198.2 $ 1,573.0 $ 371.6 $ 2,082.0 $ 357.7

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ASPEN INSURANCE HOLDINGS LIMITED

SCHEDULE IV - REINSURANCEFor the Twelve Months Ended December 31, 2020, 2019 and 2018

Premiums Written Direct Assumed Ceded Net Amount ($ in millions)2020 $ 2,042.8 $ 1,660.8 $ (1,120.7) $ 2,582.92019 $ 1,956.9 $ 1,485.5 $ (1,014.5) $ 2,427.92018 $ 1,951.2 $ 1,495.7 $ (1,364.9) $ 2,082.0

Premiums Earned

Gross Amount

Assumed From Other

CompaniesCeded to Other

Companies Net Amount

Percentage ofAmountAssumed

to Net ($ in millions, except for percentages)2020 $ 2,027.1 $ 1,616.4 $ (1,110.9) $ 2,532.6 63.8 %2019 $ 1,927.5 $ 1,494.9 $ (1,129.1) $ 2,293.3 65.2 %2018 $ 1,940.5 $ 1,593.9 $ (1,319.7) $ 2,214.7 72.0 %

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ASPEN INSURANCE HOLDINGS LIMITED

SCHEDULE V - VALUATION AND QUALIFYING ACCOUNTSFor the Twelve Months Ended December 31, 2020, 2019 and 2018

ThefollowingtableshowsthemovementintheCompany’sbaddebtprovisionduringthetwelvemonthsendedDecember31,2020,2019and2018:

Balance at Beginning of

Year

Charged toCosts andExpenses

Charged toOther

Accounts DeductionsBalance at

End of Year Provisions for Bad Debt ($ in millions)2020 Premiumsreceivablefromunderwritingactivities $ 23.0 $ 11.0 $ — $ — $ 34.0Reinsurance $ — $ — $ — $ — $ —2019 Premiumsreceivablefromunderwritingactivities $ 16.2 $ 6.8 $ — $ — $ 23.0Reinsurance $ — $ — $ — $ — $ —2018 Premiumsreceivablefromunderwritingactivities $ 5.2 $ 11.0 $ — $ — $ 16.2Reinsurance $ — $ — $ — $ — $ —

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Item 19. Exhibit Index

(a)FinancialStatements,FinancialStatementSchedulesandExhibits

1.Financial Statements:TheConsolidatedFinancialStatementsofAspenInsuranceHoldingsLimitedandrelatedNotestheretoarelistedintheaccompanyingIndextoConsolidatedFinancialStatementsandReportsonpageF-1andarefiledaspartofthisReport.

2.Financial Statement Schedules:TheSchedulestotheConsolidatedFinancialStatementsofAspenInsuranceHoldingsLimitedarelistedintheaccompanyingIndextoSchedulestoConsolidatedFinancialStatementsonpageS-1andarefiledaspartofthisReport.

3.Exhibits:ExhibitNumber Description1.1 CertificateofIncorporationandMemorandumofAssociation(incorporatedhereinbyreferencetoexhibit3.1totheCompany’s2003Registration

StatementonFormF-1(RegistrationNo.333-110435))1.2 AlteredMemorandumofAssociation(incorporatedhereinbyreferencetoexhibit3.1oftheCompany’sCurrentReportonForm6-KfiledonJuly

29,2019)1.3 AmendedandRestatedBye-laws(incorporatedhereinbyreferencetoexhibit3.2oftheCompany’sCurrentReportonForm8-KfiledonFebruary

15,2019)3.1 Indenture, dated August 16, 2005, between the Company and Deutsche Bank Trust Company Americas, as trustee (incorporated herein by

referencetoexhibit4.3totheCompany’s2004RegistrationStatementonFormF-1(RegistrationNo.333-119-314))3.2 Third Supplemental Indenture, dated November 13, 2013, between the Company, as issuer, and Deutsche Bank Trust Company Americas, as

trustee(incorporatedhereinbyreferencetoexhibit4.1totheCompany’sCurrentReportonForm8-KfiledonNovember13,2013)3.3 Fourth Supplemental Indenture, dated June 27, 2019, between the Company and Deutsche Bank Trust Company Americas, as trustee

(incorporatedhereinbyreferencetoexhibit4.1totheCompany’sCurrentReportonForm8-KfiledonJune28,2019)3.4 FormofCertificateofDesignationsoftheCompany’s5.95%Fixed-to-FloatingRatePerpetualNon-CumulativePreferenceShares,datedMay2,

2013(incorporatedhereinbyreferencetoexhibit3.1totheCompany’sCurrentReportonForm8-KfiledonMay2,2013)3.5 Specimen Certificate for the Company’s 5.95% Fixed-to-Floating Rate Perpetual Non-Cumulative Preference Shares (incorporated herein by

referencetotheformofwhichisinexhibit4.1totheCompany’sCurrentReportonForm8-KfiledonMay2,2013)3.6 Form of Certificate of Designation of the Company’s 5.625% Perpetual Non-Cumulative Preference Shares, dated September 20, 2016

(incorporatedhereinbyreferencetoexhibit3.1totheCompany’sCurrentReportonForm8-KfiledonSeptember21,2016)3.7 SpecimenCertificate fortheCompany’s5.625%Perpetual Non-CumulativePreferenceShares(incorporatedhereinbyreferencetotheformof

whichisinexhibit4.1totheCompany’sCurrentReportonForm8-KfiledonSeptember21,2016)3.8 FormofCertificate of Designationfor theCompany’s 5.625%Perpetual Non-CumulativePreferenceSharesrepresentedbyDepositaryShares,

each such Depositary Share representing a 1/1000th interest in a 5.625%Perpetual Non-Cumulative Preference Share, dated August 13, 2019(incorporatedhereinbyreferencetoexhibit4.1totheCompany’sCurrentReportonForm6-KfiledonAugust13,2019)

3.9 FormofShareCertificate evidencingthe5.625%Perpetual Non-CumulativePreferenceSharesrepresentedbyDepositaryShares(incorporatedhereinbyreferencetoexhibit4.2totheCompany’sCurrentReportonForm6-KfiledonAugust13,2019)

3.10 DepositAgreementdatedasofAugust13,2019amongtheCompany,ComputershareInc.andComputershareTrustCompany,N.A.(incorporatedhereinbyreferencetoexhibit4.3totheCompany’sCurrentReportonForm6-KfiledonAugust13,2019)

3.11 FormofDepositaryReceipt(incorporatedhereinbyreferencetoexhibit4.4totheCompany’sCurrentReportonForm6-KfiledonAugust13,2019)

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4.1 Agreement and Plan of Merger, dated as of August 27, 2018, by and among Aspen Insurance Holdings Limited, Highlands Holdings, Ltd, andHighlandsMergerSub,Ltd(incorporatedhereinbyreferencetoexhibit2.1totheCurrentReportonForm8-KfiledonAugust28,2018)

4.2 Service Agreement, dated February 19, 2019, by and among Mark Cloutier, Aspen Insurance Holdings Limited and Aspen Bermuda Limited(incorporatedhereinbyreferencetoexhibit10.1totheCompany’sForm10-K/AfiledonApril29,2019)*

4.3 Management ConsultingAgreement, datedMarch28, 2019, betweenAspenInsuranceHoldingsLimitedandApolloManagement Holdings, L.P.(incorporatedhereinbyreferencetoexhibit10.1totheCompany’sCurrentReportonForm8-KfiledonMarch29,2019)

4.4 AspenInsuranceU.S.ServicesInc.NonqualifiedDeferredCompensationPlan(incorporatedhereinbyreferencetoexhibit10.1totheCompany’sQuarterlyReportonForm10-QforthethreemonthsendedMarch31,2014,filedonMay1,2014)*

4.5 AmendedandRestatedAspenInsuranceU.S.ServicesInc.NonqualifiedDeferredCompensationPlan(incorporatedhereinbyreferencetoexhibit10.2totheCompany’sQuarterlyReportonForm10-QforthethreemonthsendedSeptember30,2014,filedonNovember7,2014)*

4.6 Second Amended Restated Credit Agreement, dated March 27, 2017, among the Company, various subsidiaries therefor, various lenders andBarclaysBankplc,asadministrativeagent(incorporatedhereinbyreferencetoexhibit10.1totheCompany’sQuarterlyReportonForm10-QforthethreemonthsendedMarch31,2017filedonMay4,2017)

4.7 First AmendmenttoSecondAmendedandRestatedCredit AgreementdatedMarch11,2020,amongtheCompany,variouslendersandBarclaysBankplc,asadministrativeagent(incorporatedhereinbyreferencetoexhibit4.13filedwith theCompany’sAnnualReportonForm20-FfortheyearendedDecember31,2019filedonApril6,2020).

4.8 SecondAmendmenttoSecondAmendedandRestatedCreditAgreementdatedApril28,2020,amongtheCompany,variouslendersandBarclaysBankplc,asadministrativeagent,filedwiththisreport.

4.9 InsuranceLettersofCredit-MasterAgreement,datedDecember15,2003,betweenAspenBermudaLimited(formerlyknownasAspenInsuranceLimited)andCitibankIrelandFinancialServicesplc.(incorporatedhereinbyreferencetoexhibit10.2totheCompany’sCurrentReportonForm8-K,filedonOctober13,2006)

4.10 Assignment Agreement, datedOctober11, 2006, amongAspenBermudaLimited(formerly knownasAspenInsuranceLimited), Citibank, N.A.,Citibank Ireland Financial Services plc and The Bank of NewYork (incorporated herein by reference to exhibit 10.5 to the Company’s CurrentReportonForm8-K,filedonOctober13,2006)

4.11 Reinsurance Deposit Agreement, dated October 11, 2006, between Aspen Bermuda Limited (formerly known as Aspen Insurance Limited) andCitibankIrelandFinancialServicesplc.(incorporatedhereinbyreferencetoexhibit10.6totheCompany’sCurrentReportonForm8-K,filedonOctober13,2006)

4.12 Committed Letter of Credit Facility, dated July 30, 2012, between Aspen Bermuda Limited and Citibank Europe plc (incorporated herein byreferencetoexhibit10.1totheCompany’sCurrentReportonForm8-K,filedonJuly31,2012)

4.13 Committed Letter of Credit Facility, dated June 30, 2014, between Aspen Bermuda Limited and Citibank Europe plc (incorporated herein byreferencetoexhibit10.1oftheCompany’sCurrentReportonForm8-K,filedonJuly3,2014)

4.14 Committed Letter of Credit Facility, dated June 30, 2016, between Aspen Bermuda Limited and Citibank Europe plc (incorporated herein byreferencetoexhibit10.1oftheCompany’sCurrentReportonForm8-K,filedonJune30,2016)

4.15 DeedofAmendment,datedJune29,2018,betweenAspenBermudaLimitedandCitibankEuropeplc(incorporatedhereinbyreferencetoexhibit10.1totheCompany’sCurrentReportonForm8-K,filedonJuly3,2018)

4.16 DeedofAmendment,datedSeptember20,2019,betweenAspenBermudaLimitedandCitibankEuropeplc,(incorporatedhereinbyreferencetoexhibit4.21totheCompany’sAnnualReportonForm20-FfortheyearendedDecember31,2019filedonApril6,2020).

4.17 DeedofAmendment,datedJune26,2020,betweenAspenBermudaLimitedandCitibankEuropeplcfiledwiththisreport.4.18 AmendedandRestatedPledgeAgreement,datedDecember18,2014,betweenAspenBermudaLimitedandCitibankEuropeplc,assuccessorby

assignmenttoCitibank,N.A.(incorporatedhereinbyreferencetoexhibit10.1totheCompany’sCurrentReportonForm8-K,filedonDecember18,2014)

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4.19 Outsourcing Agreement, dated April 20, 2018, between Aspen Insurance UK Services Limited, Aspen Insurance U.S. Services, Inc., AspenBermudaLimitedandGenpactInternational,Inc.(incorporatedhereinbyreferencetoexhibit10.1oftheCompany’sCurrentReportonForm8-KfiledonApril26,2018)

4.20 NovationAgreement, datedJune29,2018,betweenAspenInsuranceUKServicesLimited,AspenInsuranceU.S.ServicesInc., AspenBermudaLimited,GenpactInternational,Inc.andGenpact(UK)Limited(incorporatedhereinbyreferencetoexhibit10.1oftheCompany’sCurrentReportonForm8-KfiledonJuly5,2018)

4.21 OutsourcingAgreement,datedasofAugust31,2018,betweenAspenInsuranceUKServicesLimited,AspenInsuranceU.S.ServicesInc.,AspenBermudaLimitedandCognizantWorldwideLimited(incorporatedhereinbyreferencetoexhibit10.1totheCompany’sCurrentReportonForm8-KfiledonSeptember7,2018)

8.1 SubsidiariesoftheCompany,filedwiththisreport12.1 OfficerCertificationofMarkCloutier, ChiefExecutiveOfficerofAspenInsuranceHoldingsLimited, asadoptedpursuanttoSection302ofthe

Sarbanes-OxleyActof2002,filedwiththisreport12.2 OfficerCertificationofKevinChidwick,ChiefFinancialOfficerofAspenInsuranceHoldingsLimited,asadoptedpursuanttoSection302ofthe

Sarbanes-OxleyActof2002,filedwiththisreport13.1 OfficerCertificationofMarkCloutier,ChiefExecutiveOfficerofAspenInsuranceHoldingsLimited,andKevinChidwick,ChiefFinancialOfficer

ofAspenInsuranceHoldingsLimited,pursuantto18U.S.C.Section1350,asadoptedpursuanttoSection906oftheSarbanes-OxleyActof2002,submittedwiththisreport

15.1 LetterfromKPMGLLPregardingchangeinregistrant’scertifyingaccountant101.0 ThefollowingfinancialinformationfromAspenInsuranceHoldingsLimited’sannualreportonForm20-FfortheyearendedDecember31,2020

formatted in XBRL includes: (i) Consolidated Balance Sheets; (ii) Consolidated Statements of Operations and Comprehensive Income; (iii)ConsolidatedStatementsofShareholders’Equity;(iv)ConsolidatedStatementsofCashFlows;and(v)NotestotheAuditedConsolidatedFinancialStatements,taggedasblocksoftextandindetail**

*Thisexhibitisamanagementcontractorcompensatoryplanorarrangement.**AsprovidedinRule406TofRegulationS-T,thisinformationis“furnished”herewithandnot“filed”forthepurposesofSections11and12oftheSecurities

ActandSection18oftheExchangeAct.SuchexhibitwillnotbedeemedtobeincorporatedbyreferenceintoanyfilingundertheSecuritiesActortheExchangeActunlessAspenInsuranceHoldingsLimitedspecificallyincorporatesitbyreference.

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SIGNATURE

TheregistrantherebycertifiesthatitmeetsalloftherequirementsforfilingonForm20-Fandthatithasdulycausedandauthorizedtheundersignedtosignthisannualreportonitsbehalf.

ASPEN INSURANCE HOLDINGS LIMITED

By: /s/KevinChidwick Name:KevinChidwick Title:ChiefFinancialOfficer

Date:April9,2021

iv

Execution Version

Exhibit 4.8

SECOND AMENDMENT TO SECOND AMENDED AND RESTATEDCREDIT AGREEMENT1. This SECOND AMENDMENT TO SECOND AMENDED AND RESTATED CREDIT AGREEMENT (this

“Amendment”), dated as of April 28, 2020, is among Aspen Insurance Holdings Limited (“Aspen”), the undersigned SubsidiaryBorrowers(togetherwithAspen,eacha“Borrower”andcollectivelythe“Borrowers”),theseveralbanksthatarepartieshereto,andBarclaysBankPLC,asadministrativeagent(insuchcapacity,the“AdministrativeAgent”).CapitalizedtermsusedbutnotdefinedhereinhavetherespectivemeaningssetforthintheCreditAgreement(asdefinedbelow).

2. WHEREAS, the Borrowers, various banks, the Collateral Agent and Barclays Bank PLC, as administrative agent,enteredintoaSecondAmendedandRestatedCreditAgreementdatedasofMarch27,2017,asamendedbytheFirstAmendmenttoSecondAmendedandRestatedCreditAgreementdatedasofMarch11,2020(the“CreditAgreement”);and

3. WHEREAS,thepartiesheretowishtoamendtheCreditAgreementassetforthherein;

4. NOW,THEREFORE,thepartiesheretoagreeasfollows:

1.Amendments.SubjecttoSection2below,theCreditAgreementisherebyamendedasfollows:

(a)Paragraph(b)ofSection7.1,FinancialConditionCovenants,oftheCreditAgreementisamendedtoreadinitsentiretyasfollows:

(b)ConsolidatedTangibleNetWorth.PermitConsolidatedTangibleNetWorthasatanydatetobelessthanthesumof(i) $1,891,100,000, (ii) 25%of Consolidated Net Incomeduringthe periodfromJanuary 1, 2020to andincludingsuchdate(ifpositive)and(iii)25%oftheaggregateNetCashProceedsofallissuancesbytheCompanyofsharesofitsCapitalStockduringtheperiodfromJanuary1,2020toandincludingsuchdate.

2.ConditionstoEffectiveness.ThisAmendmentshallbecomeeffectiveasofthedatehereof(the“AmendmentEffectiveDate”)when,andonlywhen,eachofthefollowingconditionsprecedentshallhavebeensatisfied:

(a) The Administrative Agent shall have received a counterpart of this Amendment executed by the Borrowers, theAdministrativeAgentandtheRequiredLenders.

(b) TherepresentationsandwarrantiesoftheBorrowerscontainedinSection4oftheCreditAgreementandintheotherLoan Documents are true and correct in all material respects as of the Amendment Effective Date, with the sameeffectasthoughmadeonsuchdate(unlessstatedtorelatesolelytoanearlierdate,inwhichcasesuchrepresentationsandwarrantiesshallbetrueandcorrectinallmaterialrespectsasofsuchearlierdate).

(c) NoDefaulthasoccurredandiscontinuingorwillresultfromtheeffectivenessofthisAmendment.

3.BorrowerRepresentations.EachBorrowerherebyrepresentsandwarrants,onandasoftheAmendmentEffectiveDate,that(i)therepresentationsandwarrantiesapplicabletosuchBorrowercontainedinSection4oftheCreditAgreementandintheotherLoanDocumentsaretrueandcorrectinallmaterialrespectsasoftheAmendmentEffectiveDate,withthesameeffectasthoughmadeonsuchdate(unlessstatedtorelatesolelytoanearlierdate,inwhichcasesuchrepresentationsandwarrantiesshallbetrueandcorrectinallmaterialrespectsasofsuchearlierdate),(ii)thisAmendmenthasbeendulyauthorized,executedanddeliveredbysuchBorrowerandconstitutesthelegal,validandbindingobligationofsuchBorrower,enforceableagainstsuchBorrowerinaccordancewithitsterms,subjecttogeneralprinciplesofequity(regardlessofwhetherconsideredinaproceedinginequityoratlaw)andtoapplicablebankruptcy,insolvency,andsimilarlawsaffectingtheenforcementofcreditors’rightsgenerallyand(iii)noDefaultshallhaveoccurredandbecontinuing,bothimmediatelybeforeandaftergivingeffecttotheapplicableprovisionsofthisAmendment.

4.ReaffirmationofLoanDocuments.EachBorroweragreesthateachLoanDocumenttowhichitisapartyremainsinfullforceandeffectandisherebyratifiedandconfirmed.TheamendmentsprovidedforhereinarelimitedtothespecificsectionsoftheCreditAgreementspecifiedhereinandshallnotconstituteaconsent,waiveroramendmentof,oranindicationoftheAdministrativeAgent’soranyLender’swillingnesstoconsenttoanyactionrequiringconsentunderanyotherprovisionoftheCreditAgreement.

5. Other. The provisions of Sections 11.5, 11.9, 11.12, 11.13 and 11.20 of the Credit Agreement are incorporated herein byreferenceasifsetforthinfullherein,mutatismutandis.

INWITNESSWHEREOF,thepartiesheretohavecausedthisAmendmenttobedulyexecutedanddeliveredbytheir properanddulyauthorizedofficersasofthedayandyearfirstabovewritten.

ASPENINSURANCEHOLDINGSLIMITED,

asaBorrower

By:/s/MarkPickering

Name:MarkPickeringTitle:GroupTreasurer

ASPENBERMUDALIMITED,

asaBorrower

By:/s/ChristianDunleavy

Name:ChristianDunleavyTitle:ChiefExecutiveOfficer

ASPENINSURANCEUKLIMITED,

asaBorrower

By:/s/MichaelCain

Name:MichaelCainTitle:Director

ASPEN(UK)HOLDINGSLIMITED,

asaBorrower

By:/s/MichaelCain

Name:MichaelCainTitle:Director

[SignaturePagetoSecondAmendmenttoSecondAmendedandRestatedCreditAgreement]

ASPENSPECIALTYINSURANCECOMPANY,

asaBorrower

By:/s/KennethCadematori

Name:KennethCadematoriTitle:CFO

ASPENU.S.HOLDINGS,INC.,

asaBorrower

By:/s/KennethCadematori

Name:KennethCadematoriTitle:CFO

ASPENUNDERWRITINGLIMITED,

asaBorrower

By:/s/StuartRiley

Name:StuartRileyTitle:Director

ASPENAMERICANINSURANCECOMPANY,

asaBorrower

By:/s/KennethCadematori

Name:KennethCadematoriTitle:CFO

[SignaturePagetoSecondAmendmenttoSecondAmendedandRestatedCreditAgreement]

BARCLAYSBANKPLC,

asAdministrativeAgentandaLender

By:/s/KarlaMaloof

Name:KarlaMaloofTitle:ManagingDirector

Executed in New York

Executed in New York

CITIBANK,N.A.,

asSyndicationAgentandaLender

By:/s/JohnModin

Name:JohnModinTitle:ManagingDirector

[SignaturePagetoSecondAmendmenttoSecondAmendedandRestatedCreditAgreement]

THEBANKOFNEWYORKMELLON,

asaLender

By:/s/MichaelPensari

Name:MichaelPensariTitle:Director

DEUTSCHEBANKAGNEWYORKBRANCH,

asaLender

By:/s/AnnieChung

Name:AnnieChungTitle:DirectorBy:/s/MingKChu

Name:MingKChuTitle:Director

[SignaturePagetoSecondAmendmenttoSecondAmendedandRestatedCreditAgreement]

LLOYDS BANK CORPORATE MARKETS PLC,asaLender

By:/s/KamalaBasdeoName:KamalaBasdeoTitle:AssistantVicePresident

By:/s/TinaWongName:TinaWongTitle:AssistantVicePresident

HSBCBANKUSA,NATIONALASSOCIATION,

asaLender

By:/s/MariaTeresaPereyraLopezName:MariaTeresaPereyraLopezTitle:VP,GlobalRelationshipBanker,

FIGInsurance

U.S.BANKNATIONALASSOCIATION,

asaLender

[SignaturePagetoSecondAmendmenttoSecondAmendedandRestatedCreditAgreement]

By:/s/GlennSchuermannName:GlennSchuermannTitle:VicePresident

[SignaturePagetoSecondAmendmenttoSecondAmendedandRestatedCreditAgreement]

Exhibit 4.17DEED OF AMENDMENT

Date: June 26, 2020Between:(1) Citibank Europe plc (“Citibank”); and(2) Aspen Bermuda Limited (the “Company”).1. Background1.1On30July2012aCommittedFacilityLetterforIssuanceofPaymentInstrumentswassignedbetweenCitibankandtheCompany,asamendedbyLettersofAmendmentdated30June2014and30June2016,andDeedsofAmendmentdated21June2018and20September2019(the“Committed Facility Letter”).1.2ThePartieshaveagreedcertainamendmentstotheCommittedFacilityLetterasdetailedinthisdeed.1.3TermsandexpressionsdefinedintheCommittedFacilityLettershallhavethesamemeaningswhenusedinthisdeedunlessthecontextotherwiserequiresorthecontraryisotherwiseindicated.1.4ThepartiestothisdeedherebyagreethatfromtheEffectiveDate(asdefinedbelow)therightsandobligationsofthepartiesundertheCommittedFacilityLetterandthetermsoftheCommittedFacilityLettershallbeamendedasspecificallysetoutbelow.2. Effective DateThefollowingamendmentsshalltakeeffectonandfrom30June2020(“Effective Date”).3. AmendmentsWitheffectfromtheEffectiveDate,thethefollowingamendmentsshallbemadetotheCommittedFacilityLetter:

1. Clause8oftheCommittedFacilityLettershallbeamendedandrestatedinitsentiretyasfollows:“ThefacilityshallonlyapplyinrespectofCreditsissuedonorpriorto30June2022(the“FacilityPeriod”).TheFacilityshallexpireontheearlierof(1)thedatethatisoneyearfromtheendoftheFacilityPeriod;or(2)thestatedexpirydateonthelastremainingCreditissuedwithintheFacilityPeriod(the“ExpiryDate”).TheBankandtheCompanyshallcommencenegotiations,withoutbeingunderanyobligation,regardingtherenewaloftheFacilityatleast60daysbeforetheendoftheFacilityPeriod.”

4. Costs and expensesEachpartytothisdeedshallbearitsowncostsandexpensesinrelationtotheamendmentsagreedpursuanttothetermsofthisdeed.5. Affirmation and acceptance5.1WitheffectfromtheEffectiveDate,thetermsandconditionsoftheCommittedFacilityLettershallbereadandconstruedbyreferencetothisdeedandallreferencestotheCommittedFacilityLettershallbedeemedtoincorporatetherelevantamendmentscontainedwithinthisdeed and all references in the Committed Facility Letter to “this Committed Facility Letter” shall with effect fromthe Effective Date bereferencestotheCommittedFacilityLetterasamendedbythisdeed.5.2IntheeventofanyconflictbetweenthetermsofthisdeedandtheCommittedFacilityLetter,thetermsofthisdeedshallprevail.5.3Fortheavoidanceofdoubt,exceptasamendedbythetermsofthisdeed,allofthetermsandconditionsoftheCommittedFacilityLettershallcontinuetoapplyandremaininfullforceandeffect.

5.4TheCompanyshall,attherequestofCitibank,doallsuchactsnecessaryordesirabletogiveeffecttotheamendmentseffectedortobeeffectedpursuanttothetermsofthisdeed.6. Continuation of SecurityTheCompanyconfirmsthat,onandaftertheEffectiveDate:(a) notwithstanding the amendments made to the Committed Facility Letter pursuant to this deed, the Amended and Restated PledgeAgreementdated18 December2014,betweentheCompanyandCitibank,asamendedfromtimetotime(the“Pledge Agreement”)andanysecuritygrantedunderitcontinuesinfullforceandeffect;andb)suchPledgeAgreementandsecurityextendstotheCommittedFacilityLetter,asamendedpursuanttothisdeed.7. CounterpartsThisdeedmaybeexecutedincounterparts,eachofwhichshallbedeemedtobeanoriginal,andallsuchcounterpartstakentogethershallconstituteoneandthesameagreement.ThisamendmentshalltakeeffectasadeednotwithstandingitissignedunderhandbyCitibank.8. Third party rightsNopersonshallhaveanyrighttoenforceanyprovisionofthisdeedundertheContracts(RightsofThirdParties)Act1999.9. Governing lawThisdeed(andanynon-contractualobligation,dispute,controversy,proceedingsorclaimofwhatevernaturearisingoutofitorinanywayrelatingtothisdeedoritsformation)shallbegovernedbyandconstruedinaccordancewithEnglishlaw.

Signatories to the deed of amendment

EXECUTED AS A DEED BY OR ON BEHALF OF THE COMPANY

andsignedbythepersonsspecifiedontherightactinginaccordancewiththelawsofBermuda,undertheauthorityoftheCompanypursuanttoaresolutionofAspenBermudaLimiteddated:June 26, 2020

Signed/s/MarkPickering

NameMarkPickering

TitleChiefFinancialOfficer

Signed/s/BryanAstwood

NameBryanAstwood

TitleChiefInvestmentOfficer

I/WE HEREBY CONFIRM OUR ACCEPTANCE ON BEHALF OF CITIBANK

By:/s/NiallTuckey

Name:NiallTuckey

th

Title:Director

Exhibit 8.1

SUBSIDIARIES OF THE COMPANY

NAME OF SUBSIDIARY JURISDICTION OF INCORPORATIONAcornLimited BermudaAspenBermudaLimited BermudaAspenCapitalManagement,Ltd BermudaAspenCatFundLimited BermudaPeregrineReinsuranceLtd BermudaSilvertonReLtd. BermudaAspenInsuranceUKLimited UnitedKingdomAspen(UK)HoldingsLimited UnitedKingdomAspen(US)HoldingsLimited UnitedKingdomAspenEuropeanHoldingsLimited UnitedKingdomAspenInsuranceUKServicesLimited UnitedKingdomAIUKTrusteesLimited UnitedKingdomAspenRiskManagementLimited UnitedKingdomAspenManagingAgencyLimited UnitedKingdomAspenUnderwritingLimited UnitedKingdomAspenUKSyndicateServicesLimited UnitedKingdomAspenRecoveriesLimited UnitedKingdomAPJAssetProtectionJerseyLimited JerseyAspenSpecialtyInsuranceSolutionsLLC CaliforniaAspenU.S.Holdings,Inc. DelawareAspenCapitalAdvisorsInc. DelawareAspenInsuranceU.S.ServicesInc. DelawareAspenReAmerica,Inc. DelawareAspenSpecialtyInsuranceManagement,Inc.

Massachusetts

AspenSpecialtyInsuranceCompany NorthDakotaAspenAmericanInsuranceCompany TexasAspenSingaporePte.Ltd. SingaporeBlueWatersInsurers,Corp. PuertoRicoAspenInsuranceIrelandHoldingsLimited Ireland

Exhibit 12.1

CERTIFICATION

I,MarkCloutier,certifythat:

1. IhavereviewedthisannualreportonForm20-FofAspenInsuranceHoldingsLimited;

2. Basedonmyknowledge,thisreportdoesnotcontainanyuntruestatementofamaterialfactoromittostateamaterialfactnecessarytomakethestatementsmade,inlightofthecircumstancesunderwhichsuchstatementsweremade,notmisleadingwithrespecttotheperiodcoveredbythisreport;

3. Basedonmyknowledge,thefinancialstatements,andotherfinancialinformationincludedinthisreport,fairlypresentinallmaterialrespectsthefinancialcondition,resultsofoperationsandcashflowsoftheregistrantasof,andfor,theperiodspresentedinthisreport;

4. Thecompany’sothercertifyingofficerandIareresponsibleforestablishingandmaintainingdisclosurecontrolsandprocedures(asdefinedinExchangeActRules13a-15(e)and15d-15(e))andinternalcontroloverfinancialreporting(asdefinedinExchangeActRules13a-15(f)and15d-15(f))forthecompanyandhave:

a) designedsuchdisclosurecontrolsandprocedures,orcausedsuchdisclosurecontrolsandprocedurestobedesignedunderoursupervision,toensurethatmaterialinformationrelatingtothecompany,includingitsconsolidatedsubsidiaries,ismadeknowntousbyotherswithinthoseentities,particularlyduringtheperiodinwhichthisreportisbeingprepared;

a) designedsuchinternalcontroloverfinancialreporting,orcausedsuchinternalcontroloverfinancialreportingtobedesignedunderoursupervision,toprovidereasonableassuranceregardingthereliabilityoffinancialreportingandthepreparationoffinancialstatementsforexternalpurposesinaccordancewithgenerallyacceptedaccountingprinciples;

b) evaluatedtheeffectivenessofthecompany’sdisclosurecontrolsandproceduresandpresentedinthisreportourconclusionsabouttheeffectivenessofthedisclosurecontrolsandprocedures,asoftheendoftheperiodcoveredbythisreportbasedonsuchevaluation;and

c) disclosedinthisreportanychangeinthecompany’sinternalcontroloverfinancialreportingthatoccurredduringtheperiodcoveredbytheannualreportthathasmateriallyaffected,orisreasonablylikelytomateriallyaffect,thecompany’sinternalcontroloverfinancialreporting.

5. Thecompany’sothercertifyingofficerandIhavedisclosed,basedonourmostrecentevaluationofinternalcontroloverfinancialreporting,tothecompany’sauditorsandtheauditcommitteeofthecompany’sboardofdirectors(orpersonsperformingtheequivalentfunctions):

a) allsignificantdeficienciesandmaterialweaknessesinthedesignoroperationofinternalcontroloverfinancialreportingwhicharereasonablylikelytoadverselyaffectthecompany’sabilitytorecord,process,summarizeandreportfinancialinformation;and

b) anyfraud,whetherornotmaterial,thatinvolvesmanagementorotheremployeeswhohaveasignificantroleintheregistrant’sinternalcontroloverfinancialreporting.

By: /s/MarkCloutier

Name: MarkCloutierDate:April9,2021 Title: ChiefExecutiveOfficer

Exhibit 12.2

CERTIFICATION

I,KevinChidwick,certifythat:

1. IhavereviewedthisannualreportonForm20-FofAspenInsuranceHoldingsLimited;

2. Basedonmyknowledge,thisreportdoesnotcontainanyuntruestatementofamaterialfactoromittostateamaterialfactnecessarytomakethestatementsmade,inlightofthecircumstancesunderwhichsuchstatementsweremade,notmisleadingwithrespecttotheperiodcoveredbythisreport;

3. Basedonmyknowledge,thefinancialstatements,andotherfinancialinformationincludedinthisreport,fairlypresentinallmaterialrespectsthefinancialcondition,resultsofoperationsandcashflowsoftheregistrantasof,andfor,theperiodspresentedinthisreport;

4. Thecompany’sothercertifyingofficerandIareresponsibleforestablishingandmaintainingdisclosurecontrolsandprocedures(asdefinedinExchangeActRules13a-15(e)and15d-15(e))andinternalcontroloverfinancialreporting(asdefinedinExchangeActRules13a-15(f)and15d-15(f))forthecompanyandhave:

a) designedsuchdisclosurecontrolsandprocedures,orcausedsuchdisclosurecontrolsandprocedurestobedesignedunderoursupervision,toensurethatmaterialinformationrelatingtothecompany,includingitsconsolidatedsubsidiaries,ismadeknowntousbyotherswithinthoseentities,particularlyduringtheperiodinwhichthisreportisbeingprepared;

b) designedsuchinternalcontroloverfinancialreporting,orcausedsuchinternalcontroloverfinancialreportingtobedesignedunderoursupervision,toprovidereasonableassuranceregardingthereliabilityoffinancialreportingandthepreparationoffinancialstatementsforexternalpurposesinaccordancewithgenerallyacceptedaccountingprinciples;

c) evaluatedtheeffectivenessofthecompany’sdisclosurecontrolsandproceduresandpresentedinthisreportourconclusionsabouttheeffectivenessofthedisclosurecontrolsandprocedures,asoftheendoftheperiodcoveredbythisreportbasedonsuchevaluation;and

d) disclosedinthisreportanychangeinthecompany’sinternalcontroloverfinancialreportingthatoccurredduringtheperiodcoveredbytheannualreportthathasmateriallyaffected,orisreasonablylikelytomateriallyaffect,thecompany’sinternalcontroloverfinancialreporting.

5. Thecompany’sothercertifyingofficerandIhavedisclosed,basedonourmostrecentevaluationofinternalcontroloverfinancialreporting,tothecompany’sauditorsandtheauditcommitteeofthecompany’sboardofdirectors(orpersonsperformingtheequivalentfunctions):

a) allsignificantdeficienciesandmaterialweaknessesinthedesignoroperationofinternalcontroloverfinancialreportingwhicharereasonablylikelytoadverselyaffectthecompany’sabilitytorecord,process,summarizeandreportfinancialinformation;and

b) anyfraud,whetherornotmaterial,thatinvolvesmanagementorotheremployeeswhohaveasignificantroleintheregistrant’sinternalcontroloverfinancialreporting.

By: /s/KevinChidwick

Name: KevinChidwickDate:April9,2021 Title: ChiefFinancialOfficer

Exhibit 13.1

CERTIFICATION PURSUANT TO18 U.S.C. SECTION 1350,

AS ADOPTED PURSUANT TOSECTION 906 OF THE SARBANES-OXLEY ACT OF 2002

InconnectionwiththisannualreportonForm20-FofAspenInsuranceHoldingsLimited(the“Company”)forthetwelvemonthsendedDecember31,2020asfiledwiththeSecuritiesandExchangeCommissiononthedatehereof(the“Report”), MarkCloutierasChiefExecutiveOfficeroftheCompanyandKevinChidwickasChiefFinancialOfficer,eachherebycertifies,pursuantto18U.S.C.§1350,asadoptedpursuantto§906oftheSarbanes-OxleyActof2002,that:

(1) theReportfullycomplieswiththerequirementsofSection13(a)or15(d)oftheSecuritiesExchangeActof1934,asamended;and(2) theinformationcontainedintheReportfairlypresents,inallmaterialrespects,thefinancialconditionandresultsofoperationsoftheCompany.

Date:April9,2021

By: /s/MarkCloutier Name: MarkCloutier Title: ChiefExecutiveOfficer

Date:April9,2021

By: /s/KevinChidwick Name: KevinChidwick Title: ChiefFinancialOfficer

KPMG LLP15 Canada SquareLondon E14 5GL United Kingdom

Private & confidentialOffice of the Chief AccountantSecurities and Exchange CommissionWashington, D.C. 20549USA9 April 2021

Ladies and Gentlemen:We are currently principal accountants for Aspen Insurance Holdings Limited and, under the date of April 9, 2021, wereported on the consolidated financial statements of Aspen Insurance Holdings Limited as of and for the years endedDecember 31, 2020 and 2019. On December 10, 2020, we were notified that Aspen Insurance Holdings Limited intendsto engage Ernst & Young LLP as its principal accountant for the year ending December 31, 2022 and that the auditor-client relationship with KPMG LLP will cease upon completion of the audit of Aspen Insurance Holdings Limited’sconsolidated financial statements as of and for the year ended December 31, 2021, and the issuance of our reportthereon. We have read Aspen Insurance Holdings Limited’s statements included under Item 16F of its Form 20-F datedApril 9, 2021, and we agree with such statements.

Yours faithfully

/s/ KPMG LLP

KPMG LLPLondonUnited Kingdom

KPMG LLP, a UK limited liability partnership and a member firm of the KPMG global organisation of independent member firms affiliated with KPMG International Limited, a private English company limited byguarantee.

Registered in England No OC301540Registered office: 15 Canada Square, London, E14 5GLFor full details of our professional regulation please refer to ‘Regulatory information' under ‘About’ at www.kpmg.com/uk

Document Classification - KPMG Confidential