Debugging over Wi-Fi has been unreliable for a long time, which can significantly slow watchOS development. I’m a longtime Apple fan, but this has been frustrating.

Simple workaround:

Turn on a hotspot on your Mac and connect both the Apple Watch and its paired iPhone to it. After that, debugging generally works again.

XCode 16.4, watchOS several from 8-11, OSX 15.6.1