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1 Penetration Testing

2 Background HSBC DOD VA Masters in Computer Science Somerset Recon Avid CTF Competitor

3 Table Of Contents 0. Information Security Risks 1. Why Pentest 2. Pentest Methodology/Process 3. Types Of Pentests 4. Pentest Tips, Tricks and Examples 5. Making Hackers Lives More Difficult 6. Get More Value Out Of Pentests 7. Questions

4 Information Security Risks

5 Information Security Risks

6 Information Security Risks Ukraine Blackout

7 Pentest Methodology/Process Pre-Engagement NDA, Rules of Engagment, Contract, Documentation Information Gathering and Reconnaissance Enumeration Vulnerability Analysis Exploitation Post Exploitation Reporting Retest

8 Why Pentest? Mitigate Risk Legal and Compliance PCI-DSS HIPPA GLBA FISMA/NIST Validate/Invalidate Security Controls Find and Mitigate Vulnerabilities Prevent compromise Make it more difficult for hackers

9 Whitebox Greybox Blackbox Internal Assessment External Assessment

10 Nework Web Mobile Device Wireless Red Team

11 Nework

12 Nework (Information Gathering)

13 Nework (Enumeration)

14 Nework (Vulenrability Analysis)

15 Nework (Exploitation)

16 Nework (Post Exploitation)

17 Web (Information Gathering)

18 Web (Enumeration/Vulnerability Analysis)

19 Web (Enumeration/Vulnerability Analysis)

20 Web (Exploitation)

21 Mobile (Information Gathering)

22 Mobile (Enumeration/Vulnerability Analysis)

23 Mobile (Exploitation)

24 Device (Information Gathering)

25 Device (Enumeration/Vulnerability Analysis)

26 Device (Exploitation)

27 Red Team (Information Gathering)

28 Read Team (Exploitation)

29 Read Team (Post Exploitation)

30 Wireless

31 Wireless

32 Pentest Tips and Tricks What are the most common passwords?

33 Pentest Tips and Tricks What are the most common passwords? password qwerty

34 Pentest Tips and Tricks Antivirus Bypass IDS/IPS/WAF Bypass NAC/WiFi/Proxy

35 Pentest Tips and Tricks Automation Nessus Nexpose Web Inspect IBM Appscan NTO Spider Acunetix Burp Suite Pro

36 Pentest Tips and Tricks Manual Pentest Automated Scan Try not to burn yourself with the soldering iron

37 Pentest Tips and Tricks Client-Side Exploitation Scope Social Engineering Screenshots Take them immediately Be careful when performing authenticated attacks or scans Eliminate false positives Document mitigations

38 Pentest Tips and Tricks Social Engineering Nobody can resist pizza Emergency Helpdesk Leveraging relationships CallerID Spoofing Spring Break 2016

39 Pentest Tips and Tricks Reporting Vulnerability description Vulnerability risk ratings Steps to reproduce Screenshots Impact Mitigations

40 Making Hackers Lives More Difficult Updated Software Segregated Networks (VLANS/Firewall rules) Hardened OS configurations Microsoft Enhanced Mitigation Experience Toolkit (EMET) Secure Software Development Lifecycles Browser Hardening (NoScript, Scriptno, Adblock Plus, Java and flash are uninstalled) Application Whitelisting Firmware/chip protections Hardware debugging is disabled

41 Get More Value Out Of Pentest Give more information to the testers Network diagrams External and internal network access 2 of every types of account Directory listings Sourcecode Web services documentation Development build of mobile application and production build Look for signs of highly skilled testers Nessus or Nexpose is not the only tool in their arsenal Manual testing Testers have additional skills/experience (exploit development, reverse engineering, software development, network, systems administration,

42 Get More Value Out Of Pentest Pentest on non production systems Development QA Pre-production Provide technical assistance to testers if needed System goes down Account gets locked out or expires Answer questions (e.g. Should user X be able to get to data Y? Is anyone using this service?) Embedded device fails

43 Get More Value Out Of Pentest How much do pentests cost? $125-$400 per hour per tester Typical engagements Web: 4-6 days Network: 4-10 days Mobile: 5-10 days Device/IoT: 7-15 Red Team: 4-10 Be careful of vulnerability scans that charge by IP address

44 Questions???

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