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Setting time is not working for Apple Watch simulator
Setting a custom time for the Apple Watch simulator is not working.

I think this is because simctl
can't, when I tried for example running xcrun simctl status_bar booted override --time "10:09 AM"
with only an Apple Watch simulator running then nothing happened. I filed this in Feedback Assistant (FB7671440), if you can reproduce it on your end too can you duplication the submission so that it rises on Apple's priority list?
It looks like this also broke with Xcode Version 14.1 (14B47b) for iPhone simulators too.
My duplicate feedback for watchOS: FB11859744 - Simulator: watchOS simulator not responding to simctl set time
New for iOS: FB11859751 - Simulator: iOS simulator not responding to simctl set time
As a workaround launch the simulator with the following environment variable: SIMCTL_CHILD_SIMULATOR_RUNTIME_VERSION=16.0 xcrun simctl boot "iPhone 14 Pro"
More information here, thanks to @saagarjha.