Cracking software with AI

Sun, 20 Sep 2026 00:00:00 +0000

In my last post I used an LLM agent to unpack live malware, which got me thinking: can LLMs also crack software?

Let’s find out.

Cracking a crackme

To have something to crack, I built a simple VM-based crackme with GPT-6 Astra that takes a flag, does some basic transforms on it, and checks the result against a hardcoded, obfuscated value. Not too hard, but not trivial and most importantly, the solution for it is not in the model’s weights.

Unpacking malware with AI (safely)

Fri, 18 Sep 2026 00:00:00 +0000

In my last post, I showed how to unpack a random malware sample I found online. In this post, I’ll show how to let an AI agent do it - safely, with a real sandbox that neither the malware nor the agent can escape.
(Contrary to popular belief, it’s possible.)

Sandboxing setup

Handling malware is very dangerous, so you need a VM. Easy.

Using AI agents on their own has some limited risk - they can accidentally run $ rm -rf /, or just do other accidental stuff that they shouldn’t. In a regular project, the LLM risk is really not that high, as most errors are harmless or recoverable.

Ai on AP Security

Cracking software with AI

Cracking a crackme

Unpacking malware with AI (safely)

Sandboxing setup