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  • The Pentester Blueprint

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    This document provides an overview of becoming a penetration tester or pentester. It discusses that pentesting involves assessing security from an adversarial perspective by attempting to exploit vulnerabilities. The document outlines skills needed like technological knowledge of networking, operating systems, security and applications as well as hacking knowledge. It recommends building a home lab with virtual machines to practice penetration testing techniques. The document provides various learning resources and certifications someone can pursue to become a pentester.

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    This document provides an overview of becoming a penetration tester or pentester. It discusses that pentesting involves assessing security from an adversarial perspective by attempting to exploit vulnerabilities. The document outlines skills needed like technological knowledge of networking, operating systems, security and applications as well as hacking knowledge. It recommends building a home lab with virtual machines to practice penetration testing techniques. The document provides various learning resources and certifications someone can pursue to become a pentester.

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    1K views27 pages

    The Pentester Blueprint

    Uploaded by

    james smith
    This document provides an overview of becoming a penetration tester or pentester. It discusses that pentesting involves assessing security from an adversarial perspective by attempting to exploit vulnerabilities. The document outlines skills needed like technological knowledge of networking, operating systems, security and applications as well as hacking knowledge. It recommends building a home lab with virtual machines to practice penetration testing techniques. The document provides various learning resources and certifications someone can pursue to become a pentester.

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    of 27

    The Pentester Blueprint:

    A Guide to Becoming a Pentester


    whoami:
    Phillip Wylie, CISSP, OSCP, GWAPT
    Principal Pentester @ US Bank
    Adjunct Professor @ Richland College
    Ambassador @ Bugcrowd
    The Pwn School Project Founder
    • 21+ years IT and InfoSec experience
    • 6+ years system administration
    • 8 years network security & AppSec
    • 7 years pentesting (5 years consulting)
    "With great power
    comes great
    responsibility."
    -Voltaire
    Only hack if you have permission and even
    better written permission. Hacking
    without permission is illegal.
    What Is Pentesting?
    • Assessing security from an adversarial
    perspective, attempting to exploit
    vulnerabilities to gain unauthorized access to
    systems and sensitive data (aka hacking).
    Why Pentesting?
    Security posture from an adversarial
    perspective
    • Better understanding of security risk severity
    • Exploitable vulnerabilities are higher risk and
    a higher priority for remediation as well as
    justification for budgeting.
    Why Pentesting?
    • Regulatory Compliance - Required for PCI DSS
    (Payment Card Industry Data Security Standard)
    • Fun job
    • A lot of job opportunities
    Pentesting Jobs
    • Penetration Testers aka Pentesters
    • Security Consultants, Analysts and
    Engineers
    Pentesting Synonyms
    • Ethical Hackers
    • Offensive Security
    • Adversarial Security
    • Threat and Vulnerability Management
    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
    Types of Pentests:
    Targets
    • Network – Internal, External, Wireless
    • Application – Web App, Thick Client, Mobile,
    Cloud
    • Hardware –Network Hardware (routers, switches,
    etc.),IoT (Internet of Things), Medical Devices
    (pacemakers, insulin pumps, etc.)
    • Transportation – Vehicles of all types
    • People – Social Engineering
    • Buildings – Physical Security (often Included
    in Social Engineering
    Types of Pentests:
    Target Knowledge
    • Black Box – limited to target IP’s, more of an
    attacker approach
    • White Box (aka Crystal Box) – detailed system
    info including accounts for app testing,
    documentation
    • Gray Box – partial knowledge of target, A cross
    Between the other two methods
    Types of Tests: Testing
    Depth
    • Vulnerability Scans – just running
    a vulnerability scanner.
    • Vulnerability Assessments –
    vulnerability scanning plus vulnerability
    validation.
    • Pentest – Vulnerability Test plus exploitation
    (aka hacking)
    • Red Team/Adversarial Tests – testing blue
    teams, attack simulation, less restrictive
    scope
    Specializations
    • Generalist – Network, WiFi, Light Web App
    • Application – Web App, Mobile, Thick
    Client
    • Social Engineering - People
    • Physical - Buildings
    • Transportation – Vehicles, Airplanes
    • Red Team – Adversarial Simulation
    How Do I Become a
    Pentester?
    Technological Knowledge
    • Network
    • Operating Systems (especially Windows and
    Linux)
    • Security
    • Application
    • Hardware
    How Do I Become a
    Pentester?
    Hacking Knowledge
    • Classes
    • Conferences
    • Meetings/Meetups
    • Self-Study
    • Home labs
    • Videos
    • Tutorials
    • Blogs and Articles
    • Twitter
    How Do I Become a
    Pentester?
    Hacker Mindset
    The Hacker Mindset is the ability to think like a
    hacker and be able to find ways to exploit
    vulnerabilities. The Hacker Mindset is a culmination
    of creative and analytical thinking. Developing this
    mindset is similar to learning how to troubleshoot.

    The Hacker Mindset takes time and repetition to


    develop and is best developed by hands on hacking
    experience.
    Pentester Blueprint
    Formula

    Technology Knowledge
    +
    Security Knowledge
    +
    Hacker Mindset
    Where to start?

    ?
    Developing a Plan

    Filling the Gaps


    • 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 (capture The Flag) and
    bug bounties
    • Everyone: Build a lab!
    Lab
    • Minimalist Lab – Virtualized Hosts (aka VMs)
    using VMWare, VirtualBox, Hypervisor, Etc.
    • Dedicated Lab – Computer dedicated to lab
    purposes with VMs
    • Advanced Lab – Servers, computers, routers and
    switches
    Home Lab:
    Attack Platform

    • Kali Linux
    • Parrot OS (Linux)
    • Ubuntu w/ Pen Tester Framework (PTF)
    • Windows 10 w/ Commando VM
    Home Lab:
    Targets
    • Create VM (Virtual Machine) Targets using VulnHub.com
    • Metasploitable 2 & 3
    • OWASP Webgoat
    • Create your own VM Targets with vulnerable software from
    Exploit-DB.com
    Recommended Reading
    Penetration Testing
    A Hands-On Introduction to Hacking

    The Hackers Playbook 2 & 3

    The Web Application Hacker's


    Handbook: Discovering and Exploiting
    Security Flaws

    RTFM: Red Team Field Manual


    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

    • Bugcrowd University: bugcrowd.com/university/


    • SANS Pentesting Blog: pen-testing.sans.org/blog/
    • HackingTutorials.org
    • Cybrary.it
    • Web Security Academy: https://portswigger.net/web-security
    • owasp.org
    • Hack The Box: hackthebox.eu
    • Over The Wire CTF: overthewire.org/wargames/

    https://thehackermaker.com/learning-resources/
    Certifications
    Entry Level
    • CEH - eCCouncil
    • PenTest+ - CompTIA
    Intermediate
    • GPEN – SANS/GIAC
    • OSCP – Offensive Security
    Advanced
    • GxPN – SANS/GIAC
    • OSCE – Offensive Security
    Job Tips
    • Professional Networking
    • Community: Clubs/groups and conferences
    • LinkedIn
    • Interview Tips
    • Prepare for interviews
    • Know the OWASP Top 10
    • Be able to explain the basics like 3-way TCP
    handshake and OSI Model
    Contact

    The Pwn School Project


    /ln/PhillipWylie PwnSchool.com

    [email protected] Ethical Hacking Class &


    Web App Pentesting
    @ Richland College
    @PhillipWylie
    TheHackerMaker.com

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