Boris from the team here -- I don't think this is right. If you are able to repro in the Desktop app, could you comment back? I cannot repro.
Note: this is for Cowork, not sure if that makes a difference, I don't use the desktop app for coding.
Claude asked me a question at 12:05pm my time, came back at 12:40 and the question prompt disappeared and it spat back a message. Previously when I was writing a Google Doc, it would prompt me for questions, I'd come back and it would have timed out like this and just made a new version of the doc.