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At night he says : It's late. I need a place to sleep.  :/

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If you need to steal a ring in a cell - then no, he will not say that.

I had this issue as well, unfortunately I didn't bother to create a bug report since it seemed to resolve itself.  

Worth noting is that it wasn't triggering- [Slight Spoilers Below]

-the event when I still had the Lonely Nun quest to finish.  After finishing it, I was able to enter the Monastery at night, and get the information to track down the bandit(s).