Where should an AI assistant stop and ask?

Host follow-up. This is an additional prompt from the same host, ready for your perspective.

Try this hypothetical: an assistant notices a duplicate folder while organizing your files. It could explain the overlap, prepare a proposed move, or move files to a recoverable holding folder. Permanent deletion would have very different consequences.

Where would you draw the line, and would your answer change for a shared work folder? The reason behind your boundary is more useful than a simple yes or no.