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Introduction To Penetr ation T es ti ng Paul Asadoorian, GCIA, GCIH PaulDotCom Enterprises, LLC http://pauldotcom.com

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Page 1: In Trot Open Testing

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Introduction To

Penetration Testing

Paul Asadoorian, GCIA, GCIHPaulDotCom Enterprises, LLC

http://pauldotcom.com

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Outline

• Why should we perform assessments?

• Security Assessment classifications

• Future of security assessments

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Why Hack Yourself?

• Security assessments helporganizations to:

• Understand threats for better defense

• Determine risk to make informed ITdecisions

• Test incident handling procedures,intrusion detection systems, and othersecurity

•TSA is a good example

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Risk = Threat x Vulnerability

“Risk is a function of the likelihood of a given threat-source's 

exercising a particular potential vulnerability, and the resulting 

impact of that adverse event on the organization.” 

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Assessment Classifications

• Target Identification

• Portscanning

• Vulnerability Scanning

• Penetration Testing

• Web Application Testing• Client-Side Exploits

• Source Code Auditing

• “Ethical Hacking” Components

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Target Identification

• Local scans, use ARP

• Remote test, use common ports, be sneaky

• RDP (!), SSH known_hosts, netstat, DNS

• Tools

• Nmap - ARP scanning

• nbtscan - NetBIOS scanner, fast!

• Cain & Abel - ARP Scanner

•Superscan - Foundstone tool

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Portscanning

• Find open ports on a host

• Often includes service and OSfingerprinting

• Tools include Nmap & Nessus

PORT STATE SERVICE VERSION135/tcp open msrpc Microsoft Windows RPC445/tcp open microsoft-ds Microsoft Windows XP microsoft-ds3052/tcp open powerchute APC PowerChute Agent 6.X

Nmap In The Movies!

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Vulnerability Scanning

• Looks at the open port

• Determines the service running

• Performs more actions to determine if aservice contains known vulnerabilities

•Tools include Nessus and other specialized

applications

IT Staff can perform this testing on

their own with inProtect

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Penetration Testing

• Takes and identified port, associatedservice which contains vulnerabilities

• Uses an exploit to gain unauthorizedaccess to the target system

•Tools include Metasploit, CANVAS, &Core IMPACT

• Used to find and compile random exploits

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Web Application Testing

• Looks for vulnerabilities in webapplications on the web server

• SQL Injection• Remote File Include

• Cross-Site Scripting

• Manipulate the applications to gainunauthorized access

• Commercial tools include AppScanand WebInspect

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Client-Side Penetration

Testin• Attempts to exploit applications on a users

desktop system

• Sending email to the user with hopes theywill click a link or open an attachment

• Requires the users email address and a

server reachable from the clients• Core IMPACT is able to automate this

testing

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Source Code Auditing

• Analyze the source code of applications,looking for vulnerabilities

• Tools include DevInspect and Ounce

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Ethical Hacking

• Information Gathering

• Social Engineering

• Password Cracking (remote & local)

• War Dialing

•Wireless (WifI, Bluetooth)

• VoIP, Blackberry, Smartphones, etc...

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Future Tactics

• Attacking mobile devices,printers, cameras, access points,

wireless routers

• Protocol Attacks (WiMax,Bluetooth, EVDO, GSM)

Assessments must always continue to help analyze risk!

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/* End */

•Email: [email protected]

• Web: http://pauldotcom.com -Podcast, Blog, Mailing List, IRCChannel, Wiki