If someone wants to try it out, both Glamorous Toolkit and plain Pharo have tooling that allows integration of both local and remote LLM services.
Some links to start off with:
https://github.com/feenkcom/gt4llm
https://omarabedelkader.github.io/ChatPharo/
Edit: I suppose the next step would be to teach an LLM about "moldable exceptions", https://arxiv.org/pdf/2409.00465 (PDF), have it create its own debuggers.