I am struggling with debugging my WatchKit Extension/App on a real Apple Watch. Debugging both the iPhone App and the WatchKit Extension using the simulator the simulator is
This question has different answers. All are good.
The reason is: in my experience there are at least two different problems that prevent debugging on a real watch. Both require a different strategy.
This answer tries to help you to decide when to use which strategy.
I also had times when XCode was able to start my watch app without any help from me.
Bonus:
Starting with XCode 7.1 it seems XCode doesn't always compile all necessary Swift files (more often than before). This is not watch specific, it also applies to iOS apps. The symptoms can look similar to those of this question. -> clean your project and then restart XCode.