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[Booklist] Books for Learning (and Leveling Up) Penetration Testing

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If you’re building a serious penetration testing learning path, the right books can compress years of trial-and-error into months. Below is a curated, field-tested list—from absolute beginner to advanced red-team ops—focused on practical skills, modern tooling, and timeless fundamentals.

How to use this list

  • Pick one core track (Web, Network/Infra, or Generalist), then add one scripting title and one advanced/depth title.
  • Do the labs as you read. Reading without hands-on practice won’t stick.
  • Refresh with references. Tool bibles (Nmap, Metasploit) are worth keeping on your desk.

Beginner → Solid Foundations

  1. Penetration Testing: A Hands-On Introduction to Hacking — Georgia Weidman (No Starch)
    A classic starter that walks you through a VM lab, Kali basics, and end-to-end workflow (recon → exploit → post-ex). Still one of the most approachable on-ramps. (No Starch Press)
  2. The Pentester BluePrint — Phillip Wylie & Kim Crawley (Wiley)
    Not a “how to hack” manual—more a roadmap for breaking into the field: roles, study paths, certs, labs. Great orientation for newcomers. (Amazon)

Add one scripting title early:

  • Black Hat Python, 2nd Ed. — Justin Seitz & Tim Arnold (No Starch)
    Python 3 throughout; build offensive tools, sniffers, fuzzers, implants—everything a pentester automates weekly. (No Starch Press)

Web Application & Bug Bounty Track

  1. The Web Application Hacker’s Handbook, 2nd Ed. — Stuttard & Pinto (Wiley)
    The web-hacker’s canon. Burp-driven methodology, deep coverage of auth, input handling, logic flaws. Older, but the reasoning still trains your eye for bugs. Pair with OWASP docs for modern tech. (Wiley)
  2. Bug Bounty Bootcamp — Vickie Li (No Starch)
    Hands-on web vulns and reporting for bounty programs; bridges theory to “I can actually find and ship a report.” (No Starch Press)

Nice to have: Real-World Bug Hunting (Peter Yaworski) for annotated case studies (not listed below to keep this tight).

Network / Infrastructure & Tooling

  1. Nmap Network Scanning — Gordon “Fyodor” Lyon (Official Nmap Guide)
    From port-scan theory to NSE scripting; the official reference by Nmap’s author. A must-own desk reference. (Nmap)
  2. Metasploit: The Penetration Tester’s Guide, 2nd Ed. — Kennedy et al. (No Starch, 2025)
    Fully updated second edition: new modules, cloud assessment chapter, AD attack discussion—great for building a repeatable exploit workflow. (No Starch Press)
  3. Mastering Kali Linux for Advanced Penetration Testing, 3rd Ed. — Vijay Kumar Velu & Robert Beggs (Packt)
    Infrastructure-focused, practical labs, and up-the-stack workflows on Kali for real engagements. (Packt)

Windows & Active Directory (Enterprise Reality)

  1. Pentesting Active Directory and Windows-based Infrastructure (Packt)
    Modern AD attack surface, hands-on lab setup, and detection/defense angles alongside offense—useful beyond “just pop BloodHound.” (Packt)

Advanced Tradecraft / Red Team

  1. Advanced Penetration Testing: Hacking the World’s Most Secure Networks — Wil Allsopp (Wiley)
    Campaign-style thinking: chaining social engineering, custom malware, and bespoke exploits to simulate real adversaries. Bridges pentesting to red-team ops. (Wiley)
  2. Hands-On Hacking — Matthew Hickey & Jennifer Arcuri (Wiley)
    TTP-oriented walkthroughs to think like an adversary and practice end-to-end operations across common environments. (AbeBooks)

Specialized Depth (Pick 1)

  1. Attacking Network Protocols — James Forshaw (No Starch)
    A researcher’s view of finding bugs in protocols: capture, reverse, fuzz, exploit. If you enjoy root-cause vulnerability research, this levels you up. (No Starch Press)
  2. (Optional) The Hacker Playbook 3 — Peter Kim
    Play-by-play campaigns and checklists. Opinionated and practical; treat it like scrimmage plans for lab practice. (Amazon)

Suggested 90-Day Reading Plan (do the labs!)

Weeks 1–4

  • Weidman’s Penetration Testing (core)
  • Parallel: Black Hat Python (automate one task per chapter)
    Weeks 5–8
  • Pick your track:
    • Web: Wahh2e + Bug Bounty Bootcamp (hunt one vuln class/week)
    • Infra: Nmap Network Scanning (NSE basics) + Metasploit 2e (operator workflow)
      Weeks 9–12
  • Enterprise: Pentesting Active Directory (build mini-lab)
  • Advanced: Advanced Penetration Testing or Attacking Network Protocols (one deep-dive project)

A few notes before you dive

  • Do no harm. Only test in isolated labs or with written authorization.
  • Books age; methodology doesn’t. For older titles, apply the mindset to today’s stacks and pair with docs/changelogs.
  • Ship artifacts. Keep a hacking journal, scripts repo, and a small report template—you’ll learn faster and build a portfolio.

Sources & Edition Notes

  • No Starch Press: Black Hat Python 2e (Python 3), Penetration Testing; catalog includes new security titles. (No Starch Press)
  • Wiley: Web Application Hacker’s Handbook 2e; Advanced Penetration Testing. (Wiley)
  • Nmap official book & docs: Nmap Network Scanning (official guide). (Nmap)
  • Metasploit 2e (2025 update): publisher listings and previews. (No Starch Press)
  • Packt: Mastering Kali Linux 3e; Pentesting Active Directory and Windows-based Infrastructure. (Packt)
  • Web/bug bounty pick: Bug Bounty Bootcamp (No Starch). (No Starch Press)
  • Specialized research: Attacking Network Protocols (Forshaw). (No Starch Press)
  • Campaign playbook: The Hacker Playbook 3 (edition info). (Amazon)