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jasonnerothin
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I have a semi-reliable means of getting things up and running. Reproducible? 🤷♂️
Some combination of:
Shutdown xCode
Unplug iPhone
iPhone Settings > General > Reset > Transfer or Reset iPhone > Reset > Reset Location & Privacy
Toggle developer setting on watch: Settings > Developer (restart)
Plug in iPhone (potential long wait)
Start xCode
Re-plug iPhone (if the Xcode sync has succeeded with an error message to Trust this computer on iPhone)
The key thing seems to be Trust This Computer? on iPhone being acknowledged three times. (One for iPhone?, one for Watch?, one for Xcode? I GUESS? 🤷♂️)