I'm having the same problem, and when it occurs, the provided actions are displayed (horizontally) in reverse order.

After several months of not being able to deploy apps to my watch, and trying many things, I came across this post and tried a few things. What finally worked for me was on my iPhone going into settings, General, Transfer or Reset iPhone, Reset, Reset Location & Privacy. After that I connected my phone via USB to my MacBook and hey presto, my watch appeared in the Device list in Xcode. At the same time the Developer option finally reappeared in Settings on my watch and after a few reboots of devices everything is good again.