Xcode: Can't Install App on Apple Watch Simulator ("Will Install Watch App timed out")
I've seen this happen as well. The simulator you're trying to install to has somehow become corrupt, reseting it doesn't fix the issue. You need to go into Xcode's Devices screen, delete the affected simulator and recreate an equivalent one.
I found that these steps dramatically increase the chances of a successful install to nearly 100%:
- Uninstall the app from both Simulators (iPhone and Watch).
- Close all Simulator applications.
- Run install from Xcode.
I hope that helps!