It happened twice with the exact same scenario/results.
I have the table scheduled to sleep at 10pm and wake up at 6am.
I have the option configured to pause between tracks for 5 min.
If the table is in a pause when it goes to sleep (at 10PM) it will not wake up at 6am. I have to hit play in the app.
Yes. Say you wanted to take a photo of every track, once it completes - and after that you must hit the play button for the next track to proceed. But if it completed a track and paused before going to sleep, and you missed taking that pic, it would start the next morning and you might miss it.