Claude is pretty good at totally disregarding most of what’s in your CLAUDE.md, so I’m not optimistic. For example a project I work on gives it specific scripts to run when it runs automated tests, because the project is set up in a way that requires some special things to happen before tests will work correctly. I’ve never once seen it actually call those scripts on the first try. It always tries to run them using the typical command that doesn’t work with our setup, and I have to remind it the what correct thing to run is.
Claude is pretty good at forgetting to run maven with -am flag, writing bash with heredocs that it's interpreter doesn't weird out on, using the != operator in jq. Maybe Claude has early onset dementia.
I've had a similar experience with Gemini ignoring things I've explicitly told it (sometimes more than once). It's probably context rot. LLM give you a huge advertised number of tokens in the context, but the more stuff you put in there, the less reliably it remembers everything, which makes sense given how transformer attention blocks work internally.