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My best guess is that you are blocking the heart rate sensors which is one of the criteria it uses to determine when you are sleeping.
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@SunsetRunner Our HR trackers (Charge HR and above) use the lowering of your heart rate to determine when you're going to sleep, and help our auto-sleep recognition get precise times for start/stop.
I imagine that without the HR, it's hard to pick up a point of reference for entering sleep mode, which would explain lack of sleep. A workaround that should help would be to disable HR altogether every night before bed (tedious, but should do the trick) so that the auto-sleep tracking reverts to movement-based algorithms.
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