Keep in mind that some LLMs are better than others. I have experienced this "Aha! Now I definitely understand the problem" quite often with Gemini and GPT. Much more than I have with Claude, although not unheard of, of course... but I have went back and forth with the first two... Pasted the error -> Response from LLM "Aha! Now I definitely understand the problem" -> Pasted new error -> ... ad infinitum.