I don't mind people asking why I asked something, I'd just prefer they answer the question as well. In the original scenario, the chatbot could answer the question as written AND enquire if that's what they really meant. It's the StackOverflow syndrome where people answer a different question to the one posed. If someone asks "How can I do this on Windows?" - telling me that Windows sucks and here's how to do it on Linux is only slightly useful. Answer the question and feel free to mention how much easier it is in Linux by all means.

I personally love explaining to people who might want to solve the issue next time so I'm happy to bore them to tears if they want. But don't let us delay solving the problem this time.