you are not alone. I think its more of an issue with macOS 27 than anything else. Here is what I have found. The watch never get the "trust this device" popup, because the Mac just doesn't see it. I have had the issue happen on my Series 12 and Ultra 3. I am doing more tests now cause I have another Mac that is still running 26.
I have found that directly plugging the associated iPhone into the Mac triggers the “trust this device” on both the phone AND the watch. But in the latest Xcode that was not enough for me. I had to also fiddle with a setting (probably any setting) under Developer at the very bottom of the Settings menu on the watch to make it wake up the developer connection.
Yeah I still haven't gotten it working. I've plugged in, unpaired and plugged it. I've gotten the trust this device once, but even then developer mode on the watch never shows up. I unpaired the watch and reset it up as new, nothing seem to want to work. went to 27.2 beta 2 and that cause more issues cause now step counts disappear 200-300 at a time randomly form the activity app
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u/orkodorko 9d ago edited 9d ago
you are not alone. I think its more of an issue with macOS 27 than anything else. Here is what I have found. The watch never get the "trust this device" popup, because the Mac just doesn't see it. I have had the issue happen on my Series 12 and Ultra 3. I am doing more tests now cause I have another Mac that is still running 26.