We have encountered what appears to be a bug where an issue would not close unless a comment had been left in the comments section. There are not validators on the workflow transition to closed. Why would this be?
For humans, this is a good thing. It means that some colleague doesn't have to contact you three months later to ask why you closed it. For service accounts, it's a bit annoying but not too much.
My money is on a Behaviour making this required
Ok, check the list of Behaviours that may be active - on a very old version (before it merged with SR I think), I remember managing to set up a behaviour that would do exactly what you're seeing - it was requiring a comment during transitions, but not telling the user why it wasn't letting them proceed (because I'd made a mess of the config)
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