When I was developing my ghidra-cli tool for LLMs to use, I was using crackmes as tests and it had no problem getting through obfuscation as long as it was prompted about it. In practice when reverse engineering real software it can sometimes spin in circles for a while until it finally notices that it's dealing with obfuscated code, but as long as you update your CLAUDE.md/whatever with its findings, it generally moves smoothly from then on.

Is it also possible that crackme solutions were already in the training data?