Pentesting, or penetration testing, is one of the most exciting disciplines in the world of IT security. It’s about viewing systems through the eyes of an attacker to identify vulnerabilities before a real one does. This isn’t about “hacking for fun,” but rather a structured, often highly complex analysis of web applications, operating systems, networks, servers, and IT infrastructures. Getting started can be intimidating, but with the right resources, you can build a solid foundation. In this article, I’ll introduce you to ten excellent books that will guide you through technical pentesting in a systematic and hands-on way.
What's it about?
This book is the go-to resource for anyone focusing on web application pentesting. It provides detailed explanations of how web applications work and how typical vulnerabilities occur.
What makes it stand out?
The didactic structure is excellent: it starts with the technical basics (e.g., HTTP, cookies, sessions), then dives into classic vulnerabilities like SQL injection, XSS, session fixation, CSRF, and much more. It also covers advanced topics like WebSockets, OAuth, and client-side attacks.
Why read it?
If you want to understand how to analyze a web application systematically, this book is a must-read. It goes far beyond surface-level knowledge and teaches you the methodology of a professional web pentester.
What's it about?
This book is aimed at technically inclined readers who want to delve into exploit development. It covers buffer overflows, format string attacks, shellcode, and assembly programming.
What makes it stand out?
It’s one of the few books that explains exploit code line by line. You’ll also learn about program memory structures, registers, and debugging with GDB.
Why read it?
If you want to truly understand how exploits work under the hood, this is essential reading. Compared to “The Web Application Hacker’s Handbook,” this one focuses on low-level, system-based attacks.
What's it about?
This book is a perfect introduction to technical pentesting. It covers a broad range of topics from reconnaissance and exploitation to post-exploitation.
What makes it stand out?
The author emphasizes practical exercises. You’ll learn how to set up your own pentesting lab and get direct guidance on tools like Nmap, Metasploit, Burp Suite, and more.
Why read it?
Ideal for beginners with a technical interest. It offers a comprehensive overview of all relevant pentesting disciplines and prepares you for deeper literature.
What's it about?
Metasploit is one of the most important tools in a pentester’s toolkit. This book teaches you how to use it effectively.
What makes it stand out?
You’ll learn how to find, deploy, and combine exploits. The book also covers custom exploits, payload handling, pivoting, and post-exploitation techniques. It’s heavily focused on real-world usage.
Why read it?
Metasploit is powerful but complex. This book helps you overcome the initial learning curve and shows how to use the framework strategically.
What's it about?
A practical guide to attacking networks, servers, and applications. It closely follows real attack chains (kill chain methodology).
What makes it stand out?
The book walks you through complete attack scenarios from reconnaissance to persistence. It features current tools and methods like Empire, BloodHound, and C2 infrastructures.
Why read it?
It teaches you to plan and execute attacks like a real red teamer. Compared to Weidman’s book, this one is more suited for intermediate to advanced readers.
What's it about?
This book focuses on the art of stealthily infiltrating enterprise networks. It’s less about individual exploits and more about tactics, techniques, and procedures (TTPs).
What makes it stand out?
The focus is on “stealthy attacks.” You’ll learn how to carry out attacks undetected. It also covers social engineering, data exfiltration, and building command-and-control infrastructure.
Why read it?
If you want to simulate realistic attack scenarios, not just find vulnerabilities, this book is invaluable.
What's it about?
The book showcases real vulnerabilities discovered through bug bounty programs. You’ll learn the methodology and mindset of successful bug hunters.
What makes it stand out?
It combines technical depth with real-world examples. Many vulnerabilities can be reproduced in your own test environments.
Why read it?
Perfect for learning how to test web apps for non-obvious vulnerabilities. A great complement to “The Web Application Hacker’s Handbook.”
What's it about?
Not a classic pentesting book, but essential for understanding system hardening—and how to bypass it.
What makes it stand out?
Deep technical focus on SSH, firewalls, file systems, secure boot, and kernel protections.
Why read it?
Understanding defense means understanding attack. This book helps you spot when a target system is well-hardened—and where its weak points are.
What's it about?
A very theoretical but fundamental book: how operating systems work. Topics include memory management, scheduling, processes, and file systems.
What makes it stand out?
You’ll understand how operating systems function at a low level. Crucial for anyone interested in low-level exploitation.
Why read it?
If you understand the OS, you understand the attack surface. This book provides foundational knowledge often missing in technical pentests.
What's it about?
A hands-on book that shows how to build Bash scripts for reconnaissance, log analysis, network scanning, and exploitation.
What makes it stand out?
While many pentesting books explain tools, this one teaches you to build your own with native capabilities. Great for automation and efficiency.
Why read it?
If you want to solve repeated tasks efficiently, Bash is your best friend. This book teaches you how to build your own helpers.
Conclusion
Technical pentesting isn’t a hobby you pick up casually. It’s a complex, dynamic field that demands solid technical knowledge, curiosity, and lots of hands-on experience. The books listed here are your tools on the journey from interested beginner to professional pentester. They help you truly understand systems—not just scan them—and show that pentesting is about solving problems creatively and with technical precision.
So fire up your terminal, spin up your lab, read, understand, implement—and most importantly: stick with it.
