r/CyberSecurityAdvice • u/RespectOwn8204 • 1h ago
Are these cybersecurity books still relevant in 2026? Looking for a roadmap to get into pentesting and bug bounty
Hey everyone,
I’m currently a beginner in cybersecurity and bug bounty, and I’m seriously interested in pursuing this field professionally. I’d really appreciate some advice from people who have been working in cybersecurity, penetration testing, AppSec or bug bounty hunting for a while.
I’m particularly interested in web application security, penetration testing and bug bounty hunting, and I’m trying to figure out the best way to build a strong foundation and progress from there.
I’m considering reading the following books:
- Real World Bug Hunting: A Field Guide to Web Hacking by Peter Yaworski
- Linux Basics for Hackers, 2nd Edition by OccupyTheWeb
- Penetration Testing: A Hands On Introduction to Hacking by Georgia Weidman
- Black Hat Python, 2nd Edition by Justin Seitz and Tim Arnold
- Web Hacking 101: How to Make Money Hacking Ethically by Peter Yaworski
- Hacking: The Art of Exploitation, 2nd Edition by Jon Erickson
- The Web Application Hacker’s Handbook, 2nd Edition by Dafydd Stuttard and Marcus Pinto
- The Basics of Hacking and Penetration Testing, 2nd Edition by Patrick Engebretson
- The Hacker Playbook 3: Practical Guide to Penetration Testing by Peter Kim
- OWASP Testing Guide 4.0 by the OWASP project
- The Hacker Playbook 2: Practical Guide to Penetration Testing by Peter Kim
- Hacking: Practical Guide for Beginners by Jeff Simon
My main question is: Are these books still relevant in 2026, and will the knowledge in them remain useful over the next few years?
I understand that some of these books are quite old, especially The Web Application Hacker’s Handbook, Hacking: The Art of Exploitation and the older Hacker Playbook editions. I’m not expecting books to teach me the latest tools or every modern vulnerability, but I’m wondering whether the underlying concepts are still worth learning.
If some of these are outdated or redundant, which ones would you recommend skipping? And are there newer books or resources that would be better choices?
A little about my background
I’m a Civil Engineering graduate, so I don’t come from a traditional CS background. However, computers, programming and technology have always been a huge interest of mine.
I’ve also worked as a freelancer for around 2 years, mainly in backend development and data science.
I already have some technical foundation:
• I can code in Python and JavaScript
• I have a basic understanding of networking
• I have some Linux knowledge
• I can read and understand code in languages such as C and C++, although I’m not equally proficient in all of them
Interestingly, around 4 years ago I actually found a bug in Udemy and reported it. Unfortunately, it was marked as a duplicate 😅. But that experience really got me interested in vulnerability research.
I’ve tried learning cybersecurity through Udemy courses and YouTube, but I’ve found that many courses spend a lot of time teaching extremely basic concepts and don’t go deep enough into practical understanding. I’m looking for something more hands on and structured.
I don’t want to simply memorize tools, follow tutorials or run automated scanners without understanding what’s actually happening underneath. I want to understand how systems work, why vulnerabilities exist, how to identify them manually and eventually develop the ability to find vulnerabilities myself.
So, if you were starting from my position, what would you learn and in what order?
For example:
- What fundamentals should I learn before seriously getting into penetration testing and bug bounty?
- Which areas of networking, Linux, programming, web technologies, databases, authentication, HTTP, etc. should I be comfortable with?
- Which of the books above are still worth reading in 2026?
- Which ones are outdated, redundant or not worth my time?
- Are there any newer books, labs, platforms or other resources you would recommend?
- At what point should I start doing CTFs, labs and actual bug bounty programs?
- What would a realistic learning roadmap look like for someone with my existing background?
I’m willing to put in the time. I’m not looking for shortcuts or a quick “become a hacker in 30 days” type of roadmap. I want to build solid fundamentals and genuine practical skills.
I’d really appreciate advice from people who have actually been through this journey. Especially interested in hearing from experienced pentesters, bug bounty hunters and security researchers about what they would learn differently if they were starting today.
Thanks in advance to anyone willing to share their experience or point me in the right direction!