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Reply to Xcode says "Running .. on .. Apple Watch" all the time but never runs. Frustrating
Since this is still relevant today, I'm just bringing my grain of salt here. Unfortunately this may not work for everyone. Using the Profile function (Product > Profile / or command + i / or long press on the play button > Profile) seems to hit Xcode with a stick. When Xcode is ready with that, no need to choose a profiling template, you can stop there and run you application. I have not found the need to restart any of the devices, it looks like it's enough to make it work. However when I'm doing that a few times in a row, I may need to restart Xcode. Also in case it doesn't run automatically, you can go to your Apple Watch and open the app. It should be installed and/or updated.
Aug ’21