> and from my own experience it's very frustrating to leave a Claude session running and come back to find it did nothing because it got stuck on a question.
I cannot fathom implementing and shipping a feature to hundreds of thousands of people without even asking basic questions like: "what types of questions does Claude ask users".
Literally one of the most used plugins in their entire ecosystem, provided via their official plugin marketplace, is Superpowers. A plugin whose very first operating step is _asking numerous questions about product requirements_. Of course those prompts can't be skipped!
It wasn't even parameterized for Claude to tell the prompt what severity of question was being asked to allow at least _something_ to categorize urgency or expected response time.
Even more egregiously, 60 seconds!? The first time I noticed this happened was when it asked me a question, I turned to my second monitor to go look at some product documentation to get an answer, and by the time I turned back it had skipped me. How can I possibly provide any kind of informed answer in under 60 seconds? I can barely read some of its context for a question in 60 seconds!
I don't think they did this with malintent, but I do think this shows an enormous gap in judgement in how they handle the idea to delivery pipeline.
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.)