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The Pentester Blueprint: A Guide to Becoming a Pentester - HouSecCon

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Pentesting or ethical hacking as it is more commonly known has become a much sought-after job by people in IT, InfoSec, or those just trying to get into the industry. In this presentation Phillip Wylie shares the blueprint for becoming a pentester. The presentation combines Phillip’s experience as a pentester and ethical hacking instructor to give attendees a guide to how to pursue a career as a pentester. Phillip shares what has worked for his students and people that he has mentored over his years as a pentester. This presentation covers the knowledge and skills needed to become a pentester as well as the steps to achieve them.

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The Pentester Blueprint: A Guide to Becoming a Pentester - HouSecCon

  1. 1. The Pentester Blueprint: A Guide To Becoming a Pentester Phillip Wylie, CISSP, OSCP, GWAPT Principal InfoSec Engineer/Pentester, U.S Bank
  2. 2. whoami: PrincipalInfoSecEngineer/Pentester@USBank AdjunctProfessor(EthicalHacking)@RichlandCollege Ambassador@ Bugcrowd ThePwnSchoolProjectFounder • 21yearsITandInfoSecexperience • 6.5yearssystemadministration • 8yearsnetworksecurity&AppSec • 7yearspentesting(5yearsconsulting)
  3. 3. Onlyhackifyouhavepermission andevenbetterwritten permission.Hackingwithout permissionisillegal. "Withgreatpowercomesgreatresponsibility." -Voltaire
  4. 4. What Is Pentesting? Assessingsecurityfrom an adversarialperspective, attempting to exploit vulnerabilities to gain unauthorizedaccessto systemsand sensitive data (aka hacking).
  5. 5. Why Pentesting? Security posture from an adversarial perspective • Better understanding ofsecurity risk severity • Exploitable vulnerabilities are higherrisk and a higher priority for remediation as well as justification for budgeting. • Regulatory Compliance - Required for PCI DSS (Payment CardIndustry Data Security Standard) • Fun job with great opportunities
  6. 6. Pentesting Jobs Penetration Testers akaPentesters Security Consultants, Analysts and Engineers
  7. 7. Pentesting Synonyms • EthicalHackers • OffensiveSecurity • AdversarialSecurity • ThreatandVulnerabilityManagement
  8. 8. Pentesting Skills In Other Areas • SOC (Security Operations Center) Analysts • DFIR (Digital Forensics and Incident Response) • Network Security Analysts and Engineers • Purple Teams (where defensive and offensive security is combined) • Application Security
  9. 9. Types of Pentests: Targets –Internal, External, Wireless on – WebApp, Thick Client, Mobile, Cloud e –Network Hardware (routers, switches, etc.), net ofThings), Medical Devices (pacemakers, umps, etc.) ation –Vehicles of all types Social Engineering –Physical Security luded in Social Engineering
  10. 10. Types of Pentests: Target Knowledge –limited to target IP’s, more of an attacker approach x (aka Crystal Box) – detailed system info including forapp testing, documentation –partial knowledge of target, A cross Between the methods
  11. 11. Types of Tests: Testing Depth • Vulnerability Scans –just running a vulnerability scanner. • Vulnerability Assessments – vulnerability scanning plus vulnerability validation. • Pentest – Vulnerability Testplus exploitation (akahacking) • Red Team/Adversarial Tests –testing blue teams, attack simulation, less restrictive scope
  12. 12. How Do I Become a Pentester? Technological Knowledge • Network • Operating Systems (especially Windows and Linux) • Security • Application • Hardware
  13. 13. How Do I Become a Pentester? Hacking Knowledge • Classes • Conferences • Meetings/Meetups • Self-Study • Homelabs • Videos • Tutorials • Blogs and Articles • Twitter
  14. 14. How Do I Become a Pentester? Hacker Mindset TheHackerMindset is the ability to think like a hackerand be able to find ways to exploit vulnerabilities. TheHackerMindset is a culmination of creative and analytical thinking. Developing this mindset is similar to learning howto troubleshoot. TheHackerMindset takes time and repetition to develop and is bestdeveloped by hands on hackingexperience.
  15. 15. Pentester Blueprint Formula Technology Knowledge Security Knowledge Hacker Mindset
  16. 16. Where to Start? • No IT Experience:Start with the basics, Operating Systems, Hardware, Networking • IT Experience:Learn Linux, security and Networking • InfoSec Experience: Fill in the gaps of any basics you’re missing, start learning pentesting/ethical hacking, participate in CTFs (captureTheFlag) andbug bounties • Everyone: Build a lab!
  17. 17. Home Lab • Minimalist/Starter Lab –Virtualized Hosts (aka VMs) using VMWare,VirtualBox, Hypervisor, Etc. • Dedicated Lab – Computer dedicated to lab purposes with VMs • Advanced Lab –Servers, PCs, routers and switches
  18. 18. Home Lab:Attach Platform • Kali Linux • Ubuntu w/Pen TesterFramework (PTF) • Parrot OS • Windows 7 or10 (optional)
  19. 19. Home Lab:Targets • Create VM (Virtual Machine) Targets using VulnHub.com • Metasploitable 2 & 3 • OWASP Webgoat • Create your own VMTargets with vulnerable software from Exploit-DB.com
  20. 20. Recommended Reading • Penetration Testing: A Hands-On Introduction to Hacking • TheHackers Playbook 2 &3 • TheWeb Application Hacker's Handbook: Discovering and Exploiting Security Flaws • RTFM: Red Team Field Manual
  21. 21. Learning Resources • SANS Institute: sans.org • eLearn Security: eLearnSecurity.com • Virtual Hacking Labs: virtualhackinglabs.com • Pentester Academy: pentesteracademy.com • Pentester Lab: pentesterlab.com • Practical Pentest Labs: practicalpentestlabs.com • BugcrowdUniversity: bugcrowd.com/university/ • SANS Pentesting Blog: pen-testing.sans.org/blog/ • HackingTutorials.org • Cybrary.it • owasp.org • Hack TheBox: hackthebox.eu • OverThe Wire CTF: overthewire.org/wargames/
  22. 22. Certifications • CEH - eCCouncil • PenTest+ - CompTIA • GPEN –SANS/GIAC • OSCP– Offensive Security • GxPN –SANS/GIAC • OSCE –Offensive Security
  23. 23. Questions?
  24. 24. Phillip.Wylie@gmail.com @PhillipWylie /ln/PhillipWylie TheHackerMaker.com Thankyou!

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