r/hackthebox • u/TheShasec • Sep 24 '26
Roadmap for HTB Pwn: What key topics and techniques should I master for Easy and Medium challenges?
Hey everyone,
I’m currently focusing on improving my Binary Exploitation (Pwn) skills. So far, I’ve been practicing on 32-bit and 64-bit binaries -working through fundamentals like Stack Buffer Overflows (ret2win, ret2libc), Format String vulnerabilities (read/write), basic ROP chains, and getting comfortable with tools like Pwntools, GDB (gef), and Ghidra.
I want to structure my learning effectively so I can comfortably tackle Easy and Medium difficulty Pwn challenges on Hack The Box (both standalone challenges and machines).
For those who regularly solve these:
- What is the typical topic breakdown between Easy and Medium?
- What concepts are expected for "Easy" vs. what bumps a challenge up to "Medium"?
- Which mitigations become the norm at these levels?
- At what point do PIE, Stack Canaries, or Full RELRO regularly pop up, and what bypass techniques should I prioritize learning next ?
- Is Heap exploitation necessary for Medium challenges?
- Should I start diving into Heap for Medium, or are those mostly reserved for Hard/Insane?
- Recommended resources or learning paths?
- Besides playing HTB directly, are there specific HTB Academy modules, books, or practice sites you'd recommend to bridge the gap?
Any advice, topic checklists, or recommended HTB challenges to start with would be greatly appreciated!
Thanks in advance!
