Update: I called support who first wanted me to update to iOS14 (I can't due to app incompatibility) so they said the next steps would be to remove the tracker/device from the Fitbit app and re-pair it. This worked and I only lost 1 or 2 night's worth of sleep data (all queue up step data appeared to have transferred over) and had to re-setup my device to custom the watch face and other facets as that data is not persistent between device re-adds. Unfortunately, the same problem has occurred again ~3 times in ~1 week since I first re-paired it. This seems like either a bug or signs that my device is failing. Fingers crossed for the former.
