With Watch OS 10.1 and Xcode 15.0.1 I was facing the same issue, Developer Mode was missing. After spending the whole night the issue was my Mac's Bluetooth, it was turned off and I spent all night finding the fix. Turning Bluetooth on solved the problem. Developer Mode showes up in Privacy & Security and everything worked fine.

With Watch OS 10.1 and Xcode 15.0.1 I was facing the same issue. After spending the whole night the issue was my Mac's Bluetooth, it was turned off and I spent all night finding the fix. Turning Bluetooth on solved the problem. Developer Mode showes up in Privacy & Security and everything worked fine.