I am having the same issue -- it is pretty ridiculous that the solution is restart your watch and your phone all the time. Apple really needs to do better.

@darkpaw Unfortunately waiting 12 hours did not work (actually over 24 now). At my witts end at how developing on Apple can be this disastrous.

@darkpaw Unfortunately this did not work. Its been over a day. I can not believe how fragile developing on Apple is. Really embarrassing for a company that tries to own the entire ecosystem.