Ask your manager how they get humans to do those things, and copy that process.

So, get a bug tracker, track those bugs, tell Claude to pick tasks off it etc.

I'm not claiming this actually works, I've not tried it, I don't know how good it is for large brownfield projects, but that's the general sentiment I see.

hey claude, my users have told me that their boot.ini file is missing, was that us?

Just vibe it, let AI take the lead; follow the flow, enjoy the ride and check the result. Be the manager the bot needs; those annoying details don't have to be your concern any more.