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Introduction Guessing, Predictability and Entropy Conclusions Guessing Cryptographic Secrets and Oblivious Distributed Guessing Serdar Bozta¸ s School of Mathematical and Geospatial Sciences RMIT University August 2014 Monash University

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Page 1: Guessing Cryptographic Secrets and Oblivious Distributed ...users.monash.edu/~gfarr/research/slides/Boztas-Talk-Monash-Guess… · distribution P and taking values in Xwhich is nite

Introduction Guessing, Predictability and Entropy Conclusions

Guessing Cryptographic Secretsand

Oblivious Distributed Guessing

Serdar Boztas

School of Mathematical and Geospatial Sciences

RMIT University

August 2014Monash University

Page 2: Guessing Cryptographic Secrets and Oblivious Distributed ...users.monash.edu/~gfarr/research/slides/Boztas-Talk-Monash-Guess… · distribution P and taking values in Xwhich is nite

Introduction Guessing, Predictability and Entropy Conclusions

Outline

1 IntroductionProblem StatementOur Contribution

2 Guessing, Predictability and EntropyDefinitionsGuessing by one attackerLimited Resource GuessingPower and Memory Constrained Guessor Minimizing FailureProbabilityMultiple Memory Constrained Oblivious Guessors

3 Conclusions

Page 3: Guessing Cryptographic Secrets and Oblivious Distributed ...users.monash.edu/~gfarr/research/slides/Boztas-Talk-Monash-Guess… · distribution P and taking values in Xwhich is nite

Introduction Guessing, Predictability and Entropy Conclusions

Outline

1 IntroductionProblem StatementOur Contribution

2 Guessing, Predictability and EntropyDefinitionsGuessing by one attackerLimited Resource GuessingPower and Memory Constrained Guessor Minimizing FailureProbabilityMultiple Memory Constrained Oblivious Guessors

3 Conclusions

Page 4: Guessing Cryptographic Secrets and Oblivious Distributed ...users.monash.edu/~gfarr/research/slides/Boztas-Talk-Monash-Guess… · distribution P and taking values in Xwhich is nite

Introduction Guessing, Predictability and Entropy Conclusions

Outline

1 IntroductionProblem StatementOur Contribution

2 Guessing, Predictability and EntropyDefinitionsGuessing by one attackerLimited Resource GuessingPower and Memory Constrained Guessor Minimizing FailureProbabilityMultiple Memory Constrained Oblivious Guessors

3 Conclusions

Page 5: Guessing Cryptographic Secrets and Oblivious Distributed ...users.monash.edu/~gfarr/research/slides/Boztas-Talk-Monash-Guess… · distribution P and taking values in Xwhich is nite

Introduction Guessing, Predictability and Entropy Conclusions

Problem Statement

Let X be an unknown discrete random variable withdistribution P and taking values in X which is finite orcountable. X could represent an unknown key, IV, orpassword for a cryptosystem, or an unknown quantity ofinformation security value.

To model problems of interest, we assume that the guessor isnot all-powerful and can only ask atomic questions (e.g.,query keys/passwords) regarding singletons in X . Thiscorresponds to submitting the password and seeing if the loginis successful or not.

We assume that a sequence of questions of the formIs X = x?

are posed until the first YES answer determines the value ofthe random variable X .

Page 6: Guessing Cryptographic Secrets and Oblivious Distributed ...users.monash.edu/~gfarr/research/slides/Boztas-Talk-Monash-Guess… · distribution P and taking values in Xwhich is nite

Introduction Guessing, Predictability and Entropy Conclusions

Problem Statement

Let X be an unknown discrete random variable withdistribution P and taking values in X which is finite orcountable. X could represent an unknown key, IV, orpassword for a cryptosystem, or an unknown quantity ofinformation security value.

To model problems of interest, we assume that the guessor isnot all-powerful and can only ask atomic questions (e.g.,query keys/passwords) regarding singletons in X . Thiscorresponds to submitting the password and seeing if the loginis successful or not.

We assume that a sequence of questions of the formIs X = x?

are posed until the first YES answer determines the value ofthe random variable X .

Page 7: Guessing Cryptographic Secrets and Oblivious Distributed ...users.monash.edu/~gfarr/research/slides/Boztas-Talk-Monash-Guess… · distribution P and taking values in Xwhich is nite

Introduction Guessing, Predictability and Entropy Conclusions

Problem Statement

Let X be an unknown discrete random variable withdistribution P and taking values in X which is finite orcountable. X could represent an unknown key, IV, orpassword for a cryptosystem, or an unknown quantity ofinformation security value.

To model problems of interest, we assume that the guessor isnot all-powerful and can only ask atomic questions (e.g.,query keys/passwords) regarding singletons in X . Thiscorresponds to submitting the password and seeing if the loginis successful or not.

We assume that a sequence of questions of the formIs X = x?

are posed until the first YES answer determines the value ofthe random variable X .

Page 8: Guessing Cryptographic Secrets and Oblivious Distributed ...users.monash.edu/~gfarr/research/slides/Boztas-Talk-Monash-Guess… · distribution P and taking values in Xwhich is nite

Introduction Guessing, Predictability and Entropy Conclusions

Problem History

The link between guessing and entropy was popularized byJames L. Massey in the early 1990s. If X has high entropy isit hard to Guess? Is Shannon entropy the right measure?

The problem of bounding the expected number of guesses interms of Renyi entropies was investigated by Erdal Arikan inthe context of sequential decoding. Arikan used the HolderInequality to obtain his bound.

John Pliam independently investigated the relationshipbetween entropy, “guesswork” and security.

Boztas improved Arikan’s bound and presented other tighterbounds for specific cases.

The concept of “guessing entropy” has (i) been adopted byNIST as a measure of password strength; and (ii) also appliedby others to graphical passwords.

Page 9: Guessing Cryptographic Secrets and Oblivious Distributed ...users.monash.edu/~gfarr/research/slides/Boztas-Talk-Monash-Guess… · distribution P and taking values in Xwhich is nite

Introduction Guessing, Predictability and Entropy Conclusions

Problem History

The link between guessing and entropy was popularized byJames L. Massey in the early 1990s. If X has high entropy isit hard to Guess? Is Shannon entropy the right measure?

The problem of bounding the expected number of guesses interms of Renyi entropies was investigated by Erdal Arikan inthe context of sequential decoding. Arikan used the HolderInequality to obtain his bound.

John Pliam independently investigated the relationshipbetween entropy, “guesswork” and security.

Boztas improved Arikan’s bound and presented other tighterbounds for specific cases.

The concept of “guessing entropy” has (i) been adopted byNIST as a measure of password strength; and (ii) also appliedby others to graphical passwords.

Page 10: Guessing Cryptographic Secrets and Oblivious Distributed ...users.monash.edu/~gfarr/research/slides/Boztas-Talk-Monash-Guess… · distribution P and taking values in Xwhich is nite

Introduction Guessing, Predictability and Entropy Conclusions

Problem History

The link between guessing and entropy was popularized byJames L. Massey in the early 1990s. If X has high entropy isit hard to Guess? Is Shannon entropy the right measure?

The problem of bounding the expected number of guesses interms of Renyi entropies was investigated by Erdal Arikan inthe context of sequential decoding. Arikan used the HolderInequality to obtain his bound.

John Pliam independently investigated the relationshipbetween entropy, “guesswork” and security.

Boztas improved Arikan’s bound and presented other tighterbounds for specific cases.

The concept of “guessing entropy” has (i) been adopted byNIST as a measure of password strength; and (ii) also appliedby others to graphical passwords.

Page 11: Guessing Cryptographic Secrets and Oblivious Distributed ...users.monash.edu/~gfarr/research/slides/Boztas-Talk-Monash-Guess… · distribution P and taking values in Xwhich is nite

Introduction Guessing, Predictability and Entropy Conclusions

Problem History

The link between guessing and entropy was popularized byJames L. Massey in the early 1990s. If X has high entropy isit hard to Guess? Is Shannon entropy the right measure?

The problem of bounding the expected number of guesses interms of Renyi entropies was investigated by Erdal Arikan inthe context of sequential decoding. Arikan used the HolderInequality to obtain his bound.

John Pliam independently investigated the relationshipbetween entropy, “guesswork” and security.

Boztas improved Arikan’s bound and presented other tighterbounds for specific cases.

The concept of “guessing entropy” has (i) been adopted byNIST as a measure of password strength; and (ii) also appliedby others to graphical passwords.

Page 12: Guessing Cryptographic Secrets and Oblivious Distributed ...users.monash.edu/~gfarr/research/slides/Boztas-Talk-Monash-Guess… · distribution P and taking values in Xwhich is nite

Introduction Guessing, Predictability and Entropy Conclusions

Problem History

The link between guessing and entropy was popularized byJames L. Massey in the early 1990s. If X has high entropy isit hard to Guess? Is Shannon entropy the right measure?

The problem of bounding the expected number of guesses interms of Renyi entropies was investigated by Erdal Arikan inthe context of sequential decoding. Arikan used the HolderInequality to obtain his bound.

John Pliam independently investigated the relationshipbetween entropy, “guesswork” and security.

Boztas improved Arikan’s bound and presented other tighterbounds for specific cases.

The concept of “guessing entropy” has (i) been adopted byNIST as a measure of password strength; and (ii) also appliedby others to graphical passwords.

Page 13: Guessing Cryptographic Secrets and Oblivious Distributed ...users.monash.edu/~gfarr/research/slides/Boztas-Talk-Monash-Guess… · distribution P and taking values in Xwhich is nite

Introduction Guessing, Predictability and Entropy Conclusions

Our Contribution

In this talk we first focus on a Single Attacker Guessing anunknown random variable X .

In this simple form, the problem is easier to state and analyze,and we revisit proofs of the early results in estimating theaverage number of guesses to determine X .

This is the quantity called “guessing entropy” by NIST. Arelated quantity defined by Pliam, which specifies the minimalnumber of guesses required to succeed with a given probabilityin guessing X is also of interest.

Page 14: Guessing Cryptographic Secrets and Oblivious Distributed ...users.monash.edu/~gfarr/research/slides/Boztas-Talk-Monash-Guess… · distribution P and taking values in Xwhich is nite

Introduction Guessing, Predictability and Entropy Conclusions

Our Contribution

In this talk we first focus on a Single Attacker Guessing anunknown random variable X .

In this simple form, the problem is easier to state and analyze,and we revisit proofs of the early results in estimating theaverage number of guesses to determine X .

This is the quantity called “guessing entropy” by NIST. Arelated quantity defined by Pliam, which specifies the minimalnumber of guesses required to succeed with a given probabilityin guessing X is also of interest.

Page 15: Guessing Cryptographic Secrets and Oblivious Distributed ...users.monash.edu/~gfarr/research/slides/Boztas-Talk-Monash-Guess… · distribution P and taking values in Xwhich is nite

Introduction Guessing, Predictability and Entropy Conclusions

Our Contribution

In this talk we first focus on a Single Attacker Guessing anunknown random variable X .

In this simple form, the problem is easier to state and analyze,and we revisit proofs of the early results in estimating theaverage number of guesses to determine X .

This is the quantity called “guessing entropy” by NIST. Arelated quantity defined by Pliam, which specifies the minimalnumber of guesses required to succeed with a given probabilityin guessing X is also of interest.

Page 16: Guessing Cryptographic Secrets and Oblivious Distributed ...users.monash.edu/~gfarr/research/slides/Boztas-Talk-Monash-Guess… · distribution P and taking values in Xwhich is nite

Introduction Guessing, Predictability and Entropy Conclusions

Our Contribution

Consider a single guessor. He can guess X in order ofdecreasing probability. Clearly this minimizes the expectednumber of guesses. How is this related to the entropy of X ?

It is tempting to have a number of different guessors workingin parallel in trying to determine X , but tricky to make thispractical and scalable if they have to keep track of what eachother is guessing–consider guessors entering and leaving thegroup performing the search.

Moreover the computational power of each participant (thusthe rate at which they can implement the guessingmechanism) can vary a great deal. These factors make thestudy of Oblivious Distributed Guessing of interest.

Page 17: Guessing Cryptographic Secrets and Oblivious Distributed ...users.monash.edu/~gfarr/research/slides/Boztas-Talk-Monash-Guess… · distribution P and taking values in Xwhich is nite

Introduction Guessing, Predictability and Entropy Conclusions

Our Contribution

Consider a single guessor. He can guess X in order ofdecreasing probability. Clearly this minimizes the expectednumber of guesses. How is this related to the entropy of X ?

It is tempting to have a number of different guessors workingin parallel in trying to determine X , but tricky to make thispractical and scalable if they have to keep track of what eachother is guessing–consider guessors entering and leaving thegroup performing the search.

Moreover the computational power of each participant (thusthe rate at which they can implement the guessingmechanism) can vary a great deal. These factors make thestudy of Oblivious Distributed Guessing of interest.

Page 18: Guessing Cryptographic Secrets and Oblivious Distributed ...users.monash.edu/~gfarr/research/slides/Boztas-Talk-Monash-Guess… · distribution P and taking values in Xwhich is nite

Introduction Guessing, Predictability and Entropy Conclusions

Our Contribution

Consider a single guessor. He can guess X in order ofdecreasing probability. Clearly this minimizes the expectednumber of guesses. How is this related to the entropy of X ?

It is tempting to have a number of different guessors workingin parallel in trying to determine X , but tricky to make thispractical and scalable if they have to keep track of what eachother is guessing–consider guessors entering and leaving thegroup performing the search.

Moreover the computational power of each participant (thusthe rate at which they can implement the guessingmechanism) can vary a great deal. These factors make thestudy of Oblivious Distributed Guessing of interest.

Page 19: Guessing Cryptographic Secrets and Oblivious Distributed ...users.monash.edu/~gfarr/research/slides/Boztas-Talk-Monash-Guess… · distribution P and taking values in Xwhich is nite

Introduction Guessing, Predictability and Entropy Conclusions

Definitions

A guessing strategy can be represented by a functionG : X → {1, 2, . . .} where G (k) equals the time index of thequestion Is X = k?.

Clearly, G must be invertible on its range {1, 2, . . .} since onlyone element may be probed at any given time by a guessor.Since the answers to the queries Is X = k? are noiseless, it isenough to ask the above question exactly once for eachk ≥ 1. Hence the mapping G must be one-to-one and onto.

Assuming that the guessor knows P she is interested inminimizing–an increasing function of–the number of questionsrequired to determine X . Formally, she wants to minimize apositive moment E[G ρ] (mostly ρ = 1 is of interest) where

E[G ρ] =∑x∈X

P(x)G (x)ρ =∑k≥1

kρP(G−1(k)).

Page 20: Guessing Cryptographic Secrets and Oblivious Distributed ...users.monash.edu/~gfarr/research/slides/Boztas-Talk-Monash-Guess… · distribution P and taking values in Xwhich is nite

Introduction Guessing, Predictability and Entropy Conclusions

Definitions

A guessing strategy can be represented by a functionG : X → {1, 2, . . .} where G (k) equals the time index of thequestion Is X = k?.

Clearly, G must be invertible on its range {1, 2, . . .} since onlyone element may be probed at any given time by a guessor.Since the answers to the queries Is X = k? are noiseless, it isenough to ask the above question exactly once for eachk ≥ 1. Hence the mapping G must be one-to-one and onto.

Assuming that the guessor knows P she is interested inminimizing–an increasing function of–the number of questionsrequired to determine X . Formally, she wants to minimize apositive moment E[G ρ] (mostly ρ = 1 is of interest) where

E[G ρ] =∑x∈X

P(x)G (x)ρ =∑k≥1

kρP(G−1(k)).

Page 21: Guessing Cryptographic Secrets and Oblivious Distributed ...users.monash.edu/~gfarr/research/slides/Boztas-Talk-Monash-Guess… · distribution P and taking values in Xwhich is nite

Introduction Guessing, Predictability and Entropy Conclusions

Definitions

A guessing strategy can be represented by a functionG : X → {1, 2, . . .} where G (k) equals the time index of thequestion Is X = k?.

Clearly, G must be invertible on its range {1, 2, . . .} since onlyone element may be probed at any given time by a guessor.Since the answers to the queries Is X = k? are noiseless, it isenough to ask the above question exactly once for eachk ≥ 1. Hence the mapping G must be one-to-one and onto.

Assuming that the guessor knows P she is interested inminimizing–an increasing function of–the number of questionsrequired to determine X . Formally, she wants to minimize apositive moment E[G ρ] (mostly ρ = 1 is of interest) where

E[G ρ] =∑x∈X

P(x)G (x)ρ =∑k≥1

kρP(G−1(k)).

Page 22: Guessing Cryptographic Secrets and Oblivious Distributed ...users.monash.edu/~gfarr/research/slides/Boztas-Talk-Monash-Guess… · distribution P and taking values in Xwhich is nite

Introduction Guessing, Predictability and Entropy Conclusions

Definitions

The Renyi entropy of order α of X is defined as

Hα(X ) =log(∑

X∈Y P(X )α)

1− αα ∈ [0, 1) ∪ (1,∞),

and is a generalization of the Shannon entropy

H(X ) = −∑X∈X

P(X ) log(P(X ))

and obeys limα→1 Hα(X ) = H(X ) as well as being strictlydecreasing in α unless X is uniform on its support.

Tsallis and other entropies also connected with Renyi entropy.Most entropies lack one or more of the nice properties ofShannon entropy, but can be useful in special settings.

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Introduction Guessing, Predictability and Entropy Conclusions

Definitions

The Renyi entropy of order α of X is defined as

Hα(X ) =log(∑

X∈Y P(X )α)

1− αα ∈ [0, 1) ∪ (1,∞),

and is a generalization of the Shannon entropy

H(X ) = −∑X∈X

P(X ) log(P(X ))

and obeys limα→1 Hα(X ) = H(X ) as well as being strictlydecreasing in α unless X is uniform on its support.

Tsallis and other entropies also connected with Renyi entropy.Most entropies lack one or more of the nice properties ofShannon entropy, but can be useful in special settings.

Page 24: Guessing Cryptographic Secrets and Oblivious Distributed ...users.monash.edu/~gfarr/research/slides/Boztas-Talk-Monash-Guess… · distribution P and taking values in Xwhich is nite

Introduction Guessing, Predictability and Entropy Conclusions

Guessing by one attacker

Guess every value of X one by one in order of decreasingprobability, when the distribution P(x) is known.

Theorem

(Arikan) For all ρ ≥ 0, a guessing algorithm for X obeys the lowerbound

E[G (X )ρ] ≥[∑M

k=1 PX (xk)1/(1+ρ)]1+ρ

(1 + ln M)ρ,

while an optimal guessing algorithm for X satisfies the upper bound

E[G (X )ρ] ≤

[M∑k=1

PX (xk)1/(1+ρ)

]1+ρ.

Page 25: Guessing Cryptographic Secrets and Oblivious Distributed ...users.monash.edu/~gfarr/research/slides/Boztas-Talk-Monash-Guess… · distribution P and taking values in Xwhich is nite

Introduction Guessing, Predictability and Entropy Conclusions

Guessing by one attacker

Guess every value of X one by one in order of decreasingprobability, when the distribution P(x) is known.

Theorem

(Arikan) For all ρ ≥ 0, a guessing algorithm for X obeys the lowerbound

E[G (X )ρ] ≥[∑M

k=1 PX (xk)1/(1+ρ)]1+ρ

(1 + ln M)ρ,

while an optimal guessing algorithm for X satisfies the upper bound

E[G (X )ρ] ≤

[M∑k=1

PX (xk)1/(1+ρ)

]1+ρ.

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Introduction Guessing, Predictability and Entropy Conclusions

Guessing by one attacker

Arikan’s bounds give

[∑M

k=1

√PX (xk)]2

(1 + ln M)≤ E[G (X )]

(a)

[M∑k=1

√PX (xk)

]2

where (a) applies to the optimal guessing sequence.

Boztas’s improved upper bound gives

E[G (X )] ≤ 1

2

[M∑k=1

√PX (xk)

]2+

1

2= 2H1/2(X )−1 +

1

2

for a more general class of guessing sequences. These providean operational definition of Renyi entropy of order 1/2.

Page 27: Guessing Cryptographic Secrets and Oblivious Distributed ...users.monash.edu/~gfarr/research/slides/Boztas-Talk-Monash-Guess… · distribution P and taking values in Xwhich is nite

Introduction Guessing, Predictability and Entropy Conclusions

Guessing by one attacker

Arikan’s bounds give

[∑M

k=1

√PX (xk)]2

(1 + ln M)≤ E[G (X )]

(a)

[M∑k=1

√PX (xk)

]2

where (a) applies to the optimal guessing sequence.

Boztas’s improved upper bound gives

E[G (X )] ≤ 1

2

[M∑k=1

√PX (xk)

]2+

1

2= 2H1/2(X )−1 +

1

2

for a more general class of guessing sequences. These providean operational definition of Renyi entropy of order 1/2.

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Introduction Guessing, Predictability and Entropy Conclusions

Limited Resource Guessing

Consider a set of guessors attacking multiple targets, whosepasswords are assumed to come from the same distributionP(x).

Given P(x), how should the attacker(s) choose a distributionQ(x) in order to optimize some performance criterion, whenall the guessor(s) draw random sequential guesses from Q(x)?

In general the guessor(s) should work in parallel,independently.

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Introduction Guessing, Predictability and Entropy Conclusions

Limited Resource Guessing

Consider a set of guessors attacking multiple targets, whosepasswords are assumed to come from the same distributionP(x).

Given P(x), how should the attacker(s) choose a distributionQ(x) in order to optimize some performance criterion, whenall the guessor(s) draw random sequential guesses from Q(x)?

In general the guessor(s) should work in parallel,independently.

Page 30: Guessing Cryptographic Secrets and Oblivious Distributed ...users.monash.edu/~gfarr/research/slides/Boztas-Talk-Monash-Guess… · distribution P and taking values in Xwhich is nite

Introduction Guessing, Predictability and Entropy Conclusions

Limited Resource Guessing

Consider a set of guessors attacking multiple targets, whosepasswords are assumed to come from the same distributionP(x).

Given P(x), how should the attacker(s) choose a distributionQ(x) in order to optimize some performance criterion, whenall the guessor(s) draw random sequential guesses from Q(x)?

In general the guessor(s) should work in parallel,independently.

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Introduction Guessing, Predictability and Entropy Conclusions

Limited Memory Single Guessor

Consider a single guessor who is memory constrained andwon’t keep track of past guesses, but knows the distribution Pwhich the opponent uses to draw a single value X from X .

Define G = min{k : Xk = X} as a random variable whichdenotes the number of guesses before she is successful inexposing X . The guessor generates i.i.d. guesses X1,X2, . . . ,from X according to a distribution Q(x) with the goal ofminimizing E[G ].

Note that G = k with probability∑x∈X P(x)(1−Q(x))k−1Q(x). where k ≥ 1, by a success-fail

argument. This is because

P(G = k) =∑x∈X

P(X = x)P(G = k | X = x)

and we can use the geometric distribution with successprobability Q(x).

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Introduction Guessing, Predictability and Entropy Conclusions

Limited Memory Single Guessor

Consider a single guessor who is memory constrained andwon’t keep track of past guesses, but knows the distribution Pwhich the opponent uses to draw a single value X from X .

Define G = min{k : Xk = X} as a random variable whichdenotes the number of guesses before she is successful inexposing X . The guessor generates i.i.d. guesses X1,X2, . . . ,from X according to a distribution Q(x) with the goal ofminimizing E[G ].

Note that G = k with probability∑x∈X P(x)(1−Q(x))k−1Q(x). where k ≥ 1, by a success-fail

argument. This is because

P(G = k) =∑x∈X

P(X = x)P(G = k | X = x)

and we can use the geometric distribution with successprobability Q(x).

Page 33: Guessing Cryptographic Secrets and Oblivious Distributed ...users.monash.edu/~gfarr/research/slides/Boztas-Talk-Monash-Guess… · distribution P and taking values in Xwhich is nite

Introduction Guessing, Predictability and Entropy Conclusions

Limited Memory Single Guessor

Consider a single guessor who is memory constrained andwon’t keep track of past guesses, but knows the distribution Pwhich the opponent uses to draw a single value X from X .

Define G = min{k : Xk = X} as a random variable whichdenotes the number of guesses before she is successful inexposing X . The guessor generates i.i.d. guesses X1,X2, . . . ,from X according to a distribution Q(x) with the goal ofminimizing E[G ].

Note that G = k with probability∑x∈X P(x)(1−Q(x))k−1Q(x). where k ≥ 1, by a success-fail

argument. This is because

P(G = k) =∑x∈X

P(X = x)P(G = k | X = x)

and we can use the geometric distribution with successprobability Q(x).

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Introduction Guessing, Predictability and Entropy Conclusions

Limited Memory Single Guessor

If we apply Lagrange multipliers with the Lagrangian

J = E[G ] + λ(∑x∈X

Q(x)− 1) =∑x∈X

P(x)

Q(x)+ λ(

∑x∈X

Q(x)− 1),

we can actually show that E[G ] is minimized when we choose

Q(x) ∝√P(x)

which means that the distribution Q(x) should be “flatter” thanP(x).

Theorem

The distribution Q which minimizes the expected number ofguesses for single guessor targeting X with distribution P is

Q(x) =

√P(x)∑

y∈X√P(y)

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Introduction Guessing, Predictability and Entropy Conclusions

Limited Memory Single Guessor

Easy to check the Lagrange multipliers give minimum.

Note that if we choose Q(x) = P(x) for all x ∈ X which maylook like an attractive choice, we obtain E[G ] = |X | which issurprisingly high.

What is the minimum value of the expectation which theguessor using Proposition 1 achieves? It is

E[G ] =∑x∈X

P(x)

Q(x)=∑y∈X

√P(y)

∑x∈X

P(x)√P(x)

=[∑√

P(x)]2

= 2H1/2(X )

which provides a new operational definition of Renyi entropyof order 1/2 relating it exactly to oblivious guessing.

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Introduction Guessing, Predictability and Entropy Conclusions

Limited Memory Single Guessor

Easy to check the Lagrange multipliers give minimum.

Note that if we choose Q(x) = P(x) for all x ∈ X which maylook like an attractive choice, we obtain E[G ] = |X | which issurprisingly high.

What is the minimum value of the expectation which theguessor using Proposition 1 achieves? It is

E[G ] =∑x∈X

P(x)

Q(x)=∑y∈X

√P(y)

∑x∈X

P(x)√P(x)

=[∑√

P(x)]2

= 2H1/2(X )

which provides a new operational definition of Renyi entropyof order 1/2 relating it exactly to oblivious guessing.

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Introduction Guessing, Predictability and Entropy Conclusions

Limited Memory Single Guessor

Easy to check the Lagrange multipliers give minimum.

Note that if we choose Q(x) = P(x) for all x ∈ X which maylook like an attractive choice, we obtain E[G ] = |X | which issurprisingly high.

What is the minimum value of the expectation which theguessor using Proposition 1 achieves? It is

E[G ] =∑x∈X

P(x)

Q(x)=∑y∈X

√P(y)

∑x∈X

P(x)√P(x)

=[∑√

P(x)]2

= 2H1/2(X )

which provides a new operational definition of Renyi entropyof order 1/2 relating it exactly to oblivious guessing.

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Introduction Guessing, Predictability and Entropy Conclusions

Power and Memory Constrained Guessor MinimizingFailure Probability

Now the guesses are still i.i.d. from Q(x) but the guessor(e.g., a sensor net node) decides ahead of time that she willonly use L ∈ N guesses. We aim to find the Q(x) whichminimizes the failure probability in L guesses, namely

Pfail(L) =∑x∈X

P(x)(1−Q(x))L.

This yields the Lagrangian

J = Pfail(L) + λ(∑x∈X

Q(x)− 1)

=∑x∈X

P(x)(1−Q(x))L + λ(∑x∈X

Q(x)− 1).

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Introduction Guessing, Predictability and Entropy Conclusions

Power and Memory Constrained Guessor MinimizingFailure Probability

Now the guesses are still i.i.d. from Q(x) but the guessor(e.g., a sensor net node) decides ahead of time that she willonly use L ∈ N guesses. We aim to find the Q(x) whichminimizes the failure probability in L guesses, namely

Pfail(L) =∑x∈X

P(x)(1−Q(x))L.

This yields the Lagrangian

J = Pfail(L) + λ(∑x∈X

Q(x)− 1)

=∑x∈X

P(x)(1−Q(x))L + λ(∑x∈X

Q(x)− 1).

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Introduction Guessing, Predictability and Entropy Conclusions

Power and Memory Constrained Guessor MinimizingFailure Probability

The Lagrangian leads to the conditions

∂J

∂Q(x)= −LP(x)(1−Q(x))L−1 = −λ, ∀x ∈ X

Considering the Lagrangian and observing that L is constant,we have

Q(x) = 1− (µ/P(x))1/(L−1)

for some positive constant µ = λ/L.

The second derivative is

∂2J

∂Q(x)2= L(L− 1)P(x)(1−Q(x))L−2

and if we assume the non-degeneracy condition 0 < Q(x) < 1for all x ∈ X and L > 1 we conclude it is positive.

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Introduction Guessing, Predictability and Entropy Conclusions

Power and Memory Constrained Guessor MinimizingFailure Probability

The Lagrangian leads to the conditions

∂J

∂Q(x)= −LP(x)(1−Q(x))L−1 = −λ, ∀x ∈ X

Considering the Lagrangian and observing that L is constant,we have

Q(x) = 1− (µ/P(x))1/(L−1)

for some positive constant µ = λ/L.

The second derivative is

∂2J

∂Q(x)2= L(L− 1)P(x)(1−Q(x))L−2

and if we assume the non-degeneracy condition 0 < Q(x) < 1for all x ∈ X and L > 1 we conclude it is positive.

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Introduction Guessing, Predictability and Entropy Conclusions

Power and Memory Constrained Guessor MinimizingFailure Probability

The Lagrangian leads to the conditions

∂J

∂Q(x)= −LP(x)(1−Q(x))L−1 = −λ, ∀x ∈ X

Considering the Lagrangian and observing that L is constant,we have

Q(x) = 1− (µ/P(x))1/(L−1)

for some positive constant µ = λ/L.

The second derivative is

∂2J

∂Q(x)2= L(L− 1)P(x)(1−Q(x))L−2

and if we assume the non-degeneracy condition 0 < Q(x) < 1for all x ∈ X and L > 1 we conclude it is positive.

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Introduction Guessing, Predictability and Entropy Conclusions

Power and Memory Constrained Guessor MinimizingFailure Probability

Thus we have a minimum for Pfail(L). The normalization conditioncan be shown to yield

µ =

(|X | − 1∑

x∈X P(x)−1/(L−1)

)L−1,

thus proving:

Theorem

If the attacker is restricted to a fixed number of L ≥ 2 guesses, heroptimal oblivious strategy is to generate L i.i.d. guesses from thefollowing distribution

Q(x) = 1−

[|X | − 1∑

y∈X (P(x)/P(y))−1/(L−1)

], ∀x ∈ X

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Introduction Guessing, Predictability and Entropy Conclusions

Multiple Memory Constrained Oblivious Guessors

Consider v ≥ 2 guessors working in parallel, each drawingi.i.d. guesses from Q(x), but not coordinating their guesses. Ifthey collectively work at a rate v times the rate of the singleguessor, then ⌊

EQ[G ]

v

⌋≤ EQ[Gv ] ≤

⌈EQ[G ]

v

⌉where EQ[Gv ] denotes the expected number of guesses whenv guessors each use Q(x).

How should we optimize Q(x) once v is fixed?

Drop the subscript Q from the expectations and note that

P[Gv = k] = Pr [G ∈ [(k − 1)v + 1, kv ] ∩ Z+].

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Introduction Guessing, Predictability and Entropy Conclusions

Multiple Memory Constrained Oblivious Guessors

Consider v ≥ 2 guessors working in parallel, each drawingi.i.d. guesses from Q(x), but not coordinating their guesses. Ifthey collectively work at a rate v times the rate of the singleguessor, then ⌊

EQ[G ]

v

⌋≤ EQ[Gv ] ≤

⌈EQ[G ]

v

⌉where EQ[Gv ] denotes the expected number of guesses whenv guessors each use Q(x).

How should we optimize Q(x) once v is fixed?

Drop the subscript Q from the expectations and note that

P[Gv = k] = Pr [G ∈ [(k − 1)v + 1, kv ] ∩ Z+].

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Introduction Guessing, Predictability and Entropy Conclusions

Multiple Memory Constrained Oblivious Guessors

Consider v ≥ 2 guessors working in parallel, each drawingi.i.d. guesses from Q(x), but not coordinating their guesses. Ifthey collectively work at a rate v times the rate of the singleguessor, then ⌊

EQ[G ]

v

⌋≤ EQ[Gv ] ≤

⌈EQ[G ]

v

⌉where EQ[Gv ] denotes the expected number of guesses whenv guessors each use Q(x).

How should we optimize Q(x) once v is fixed?

Drop the subscript Q from the expectations and note that

P[Gv = k] = Pr [G ∈ [(k − 1)v + 1, kv ] ∩ Z+].

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Introduction Guessing, Predictability and Entropy Conclusions

Multiple Memory Constrained Oblivious Guessors

We obtain

E[Gv ]=∑x∈X

P(x)Q(x)∞∑k=0

(1+k)[(1−Q(x))v ]kv∑

j=1

(1−Q(x))j−1,

or

E[Gv ] =∑x∈X

P(x)Q(x)∞∑k=0

(1+k)[(1−Q(x))v ]k[

1− (1−Q(x))v

Q(x)

],

Using generation functions yields

E[Gv ] =∑x∈X

(P(x)

1− (1−Q(x))v

).

and the Lagrangian is now

Jv = E[Gv ] + λ(∑x∈X

Q(x)− 1)

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Introduction Guessing, Predictability and Entropy Conclusions

Multiple Memory Constrained Oblivious Guessors

We obtain

E[Gv ]=∑x∈X

P(x)Q(x)∞∑k=0

(1+k)[(1−Q(x))v ]kv∑

j=1

(1−Q(x))j−1,

or

E[Gv ] =∑x∈X

P(x)Q(x)∞∑k=0

(1+k)[(1−Q(x))v ]k[

1− (1−Q(x))v

Q(x)

],

Using generation functions yields

E[Gv ] =∑x∈X

(P(x)

1− (1−Q(x))v

).

and the Lagrangian is now

Jv = E[Gv ] + λ(∑x∈X

Q(x)− 1)

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Introduction Guessing, Predictability and Entropy Conclusions

Multiple Memory Constrained Oblivious Guessors

Differentiation indicates that the optimum distribution Q(x)satisfies

v(1−Q(x))v−1

(1− (1−Q(x))v )2∝ 1

P(x).

Let R(x) = 1−Q(x) which takes on values in (0, 1) but isnot a probability distribution since

∑x R(x) = |X | − 1.

Thus we have(1− R(x)v )2

vR(x)v−1∝ P(x)

and by considering the function f (u) = (1−uv )2vuv−1 on (0, 1) and

its derivative

f ′(u) = −(1− uv )[(v + 1)uv + v − 1]

vuv

we conclude that we have a minimum.

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Introduction Guessing, Predictability and Entropy Conclusions

Multiple Memory Constrained Oblivious Guessors

Differentiation indicates that the optimum distribution Q(x)satisfies

v(1−Q(x))v−1

(1− (1−Q(x))v )2∝ 1

P(x).

Let R(x) = 1−Q(x) which takes on values in (0, 1) but isnot a probability distribution since

∑x R(x) = |X | − 1.

Thus we have(1− R(x)v )2

vR(x)v−1∝ P(x)

and by considering the function f (u) = (1−uv )2vuv−1 on (0, 1) and

its derivative

f ′(u) = −(1− uv )[(v + 1)uv + v − 1]

vuv

we conclude that we have a minimum.

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Introduction Guessing, Predictability and Entropy Conclusions

Multiple Memory Constrained Oblivious Guessors

Theorem

v oblivious memory constrained attackers wanting to minimizeE[Gv ] should generate i.i.d. guesses from

Q(x) ∝[1− f −1(P(x))

].

For a distribution P for which the maximum probability is muchsmaller than one, we have

z = f (u) = (1− uv )2/(vuv−1) ≈ (1− 2u)/v

giving f −1(z) ≈ (1− vz)/2 resulting in the fast approximation

Q(x) =1 + vP(x)∑

y∈X 1 + vP(y).

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Introduction Guessing, Predictability and Entropy Conclusions

Multiple Memory Constrained Oblivious Guessors

Theorem

v oblivious memory constrained attackers wanting to minimizeE[Gv ] should generate i.i.d. guesses from

Q(x) ∝[1− f −1(P(x))

].

For a distribution P for which the maximum probability is muchsmaller than one, we have

z = f (u) = (1− uv )2/(vuv−1) ≈ (1− 2u)/v

giving f −1(z) ≈ (1− vz)/2 resulting in the fast approximation

Q(x) =1 + vP(x)∑

y∈X 1 + vP(y).

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Introduction Guessing, Predictability and Entropy Conclusions

Conclusions

Our results continue work on information theoretic problemsin the context of guessing and prediction–with applications inthe setting of security.

We have provided an alternative but exact operationaldefinition of Renyi entropy in terms of oblivious guessing.

We have generalized the guessing framework to multipleguessors, in the regime where communication betweenguessors is expensive or undesirable, such as P2P networks

Thank you for listening

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Introduction Guessing, Predictability and Entropy Conclusions

Conclusions

Our results continue work on information theoretic problemsin the context of guessing and prediction–with applications inthe setting of security.

We have provided an alternative but exact operationaldefinition of Renyi entropy in terms of oblivious guessing.

We have generalized the guessing framework to multipleguessors, in the regime where communication betweenguessors is expensive or undesirable, such as P2P networks

Thank you for listening

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Introduction Guessing, Predictability and Entropy Conclusions

Conclusions

Our results continue work on information theoretic problemsin the context of guessing and prediction–with applications inthe setting of security.

We have provided an alternative but exact operationaldefinition of Renyi entropy in terms of oblivious guessing.

We have generalized the guessing framework to multipleguessors, in the regime where communication betweenguessors is expensive or undesirable, such as P2P networks

Thank you for listening

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Introduction Guessing, Predictability and Entropy Conclusions

Conclusions

Our results continue work on information theoretic problemsin the context of guessing and prediction–with applications inthe setting of security.

We have provided an alternative but exact operationaldefinition of Renyi entropy in terms of oblivious guessing.

We have generalized the guessing framework to multipleguessors, in the regime where communication betweenguessors is expensive or undesirable, such as P2P networks

Thank you for listening

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Introduction Guessing, Predictability and Entropy Conclusions

References

E. Arikan; An Inequality on Guessing and Its Application toSequential Decoding, IEEE Transactions on Information Theory,42(1):99-105, 1996.

E. Arikan and N. Merhav; Guessing subject to distortion, IEEETransactions on Information Theory, 44(3):1041-1056, 1998.

E. Arikan and N. Merhav; Joint Source-channel Coding andGuessing with Application to Sequential Decoding, IEEETransactions on Information Theory, 44(5):1756-1769, 1998.

S. Boztas; Comments on ‘An Inequality on Guessing and ItsApplication to Sequential Decoding’, IEEE Transactions InformationTheory, 43(6):2062-2063, 1997.

S.S. Dragomir and S. Boztas; Some Estimates of the AverageNumber of Guesses to Determine a Random Variable, Proc. IEEEInternational Symposium on Information Theory, 1997.

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Introduction Guessing, Predictability and Entropy Conclusions

References (cont’d)

S.S. Dragomir and S. Boztas; Estimation of Arithmetic Means andTheir Applications in Guessing Theory, Mathematical and ComputerModelling, 28(10):31-43, 1998.

J. L. Massey; Guessing and entropy, Proc. 1994 IEEE InternationalSymposium on Information Theory, p. 204, 1994.

D. Malone, W.G. Sullivan; Guesswork and entropy, IEEETransactions Information Theory, 50(3):525- 526, 2004.

M. Feder and N. Merhav; Relations between entropy and ErrorProbability, IEEE Transactions on Information Theory40(1):259-266, 1994.

N. Merhav and E. Arikan; The Shannon Cipher System with aGuessing Wiretapper, it IEEE Transactions on Information Theory,45(6):1860-1866, 1999.

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Introduction Guessing, Predictability and Entropy Conclusions

References (cont’d)

N. Merhav, R.M. Roth, E. Arikan; Hierarchical guessing with afidelity criterion, IEEE Transactions Information Theory,45(1):330-337, 1999.

C.-E. Pfister, W.G. Sullivan; Renyi Entropy, Guesswork Moments,and Large Deviations, IEEE Transactions on Information Theory,50(11):2794, 2004.

J. O. Pliam; On the incomparability of Entropy and MarginalGuesswork in Brute-force Attacks, Proc. INDOCRYPT 2000,Lecture Notes in Computer Science 1977:67–79, 2000.

R. Sundaresan; Guessing Under Source Uncertainty, IEEETransactions on Information Theory 53(1): 269 - 287, 2007.

M. K. Hanawal and R. Sundaresan; Randomised Attacks onPasswords, Technical Report TR-PME-2010-11, and R. Sundaresan;Guessing and Compression Subject to Distortion, Technical ReportTR-PME-2010-12 ; Dept. ECE, Indian Institute of Science.http://www.pal.ece.iisc.ernet.in/PAM/docs/techreports/tech rep10/