Thanks for the reply! Disabling that setting on the DT doesn’t seem to change anything. I was only using the Clock+Transport sync in the OB plugin, Bitwig wasn’t sending it clock/transport over MIDI.
That said, I’ve noticed that disabling sync in the OB plugin and enabling it over MIDI gives me different-but-still-wrong behavior where it starts pattern playback but doesn’t sound the first note, as other users described in this thread.
So I guess the behavior I initially described is a bug in OB (maybe just with Bitwig?) and the latter is a longstanding bug when the Digitakt is slaved to anything over MIDI. This really feels like the sort of thing that should just work with a device like this. Oh well.