Yeah the UX doesn't seem great, though I do think in general the AskQuestion tool is very awkward when it gets used in a very long running process (I personally use Claude to run repetitive tests to slowly iterate on a problem and verify in true conditions that it was solved), so I wouldn't like it without the auto-continue either.

(I had originally replied on safety of letting LLMs skip questions but I don't think that was your point so I removed it.)