Developing on the watch is stupid fragile. Seriously. XCode needs to set up a secure tunnel to the watch using wifi but the watch regularly turns off or looses its wifi. There is so much magic here that like I said, embarassing to the watch team at apple.
Here are options that work for me:
The watch will often disconnect from the router even though it is on. My first solution is to go into Settings -> WiFi and make sure it is connected to the router. This works about 70% of the time. If it doesnt, you can try toggling developer mode on the watch to get to the Trust Computer which sometimes works.
Turn on your hotspot on your phone, then connect your mac and your watch to it and hope this works. You have about a 50% chance here.
If your home network is a mesh network, then make sure that the APs have handed off so that all the devices are on the same AP. I can not prove this other than through observation. So yes, turn on and off the wifi on all the devices.
Supposedly, you can actually turn on your wifi but do not connect to any router on all your devices. The networking protocol supposedly will make the connection between the Apple devices. I tried this once and I think it worked (I lose track of every voodoo dance I do).
Topic:
Developer Tools & Services
SubTopic:
General
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