HOW TO BREAK INTO PENTESTING IN 2026. COMPLETE GUIDE
Disclaimer: If it doesn't work out, don't get discouraged — I couldn't do it at the start either.
You should start right away with building practical skills because starting with theory will completely demotivate you at the beginning. You'll get all the theory necessary by practicing and researching.
Note: all of this is done by hand. Don't use tools like scanners and sqlmap, because you won't learn anything.
- pentesterlab[.]com
- https://www.hacksplaining[.]com/lessons
- Get as far as you can on http://escape.alf[.]nu/
I started solving practical tasks in my first year right here - http://www.root-me[.]org/?lang=en
- Lots of cryptography challenges https://www.mysterytwisterc3[.]org/en/
- Poke around the wargames at http://overthewire[.]org/wargames/ , going through the ordered difficulty level written on the main page. The very first wargame will let you get familiar with basic Linux commands and sort of administration.
- Another set of wargames, but on vulnerability exploitation, a bit tricky for beginners, but you can look at writeups and try to understand something. Still, it's better to try to solve it yourself and google as much info on the task topic as you can.
- For fans of reversing and those eager to grow in the reverse engineering field, I can recommend the resource https://crackmes[.]one/. You grab an easy crackme and try to solve it using IDA, Ghidra
- The tasks closest to the real world for pentesting https://www.hackthebox[.]com(
app.hackthebox.com/machines). You pick an easy box and try to solve it. The algorithm for solving any box from there is — Enumeration, Exploitation, PostExploitation, PrivilegeEscalation. It'll help you understand how to scan ports with Nmap and how to scan web applications for open files, for example, using ffuf.
- The main thing in all these tasks is to try to solve them yourself, without looking at a ready-made solution or writeup, even if it's hard and you want to give up — only this way will you learn how to work with the unknown and see things through to the end. If you're tired and out of ideas — take a break, come back to the task later.
For those who want to poke around in AD:
- https://zer1t0.gitlab[.]io/posts/attacking_ad/
- https://github[.]com/Orange-Cyberdefense/GOAD - a lab that you need to deploy yourself, fairly difficult to start with
On web vulnerabilities:
- https://portswigger[.]net/web-security/all-labs
First and foremost, work through the labs on
- SQL Injection
- Cross-site scripting
- XXE injections
- SSRF
- OS command injection
- Path traversal
- File upload vulnerabilities
This is the base. The fooooundation. Start at the APPRENTICE level and go as far as you can push.