Most of the time. I use it as my alarm. Its way better than waking up to some screeching noise scaring me to death! The only time I don't wear it when i sleep is when I have company if you know what I mean
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I have taken naps several times while wearing it. The timer/alarm feature is great for that. But I never sleep in any watch, so I havent slept with my 360. Plus I usually need a charge at night anyway...
Generally it is not a good idea to sleep with watches on, since when you sleep you can position is strange ways and a watch can put pressure on nerves and ligaments. Not a problem for everyone, of course... but it is the same reason it is a good idea to sleep in loose clothing.