I thought this was a pebble issue. I've had the pebble for over a year and it does the same thing.
You follow the same steps and everything is working again? Hmmmmmmm
My watch is at home still in its box while I'm at Disneyland. So Disneyland trumps apple in this case. Besides the fact I ordered at 12:01 but had an issue in check out. Took its time getting to me..