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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?
As a workaround launch the simulator with the following environment variable: SIMCTL_CHILD_SIMULATOR_RUNTIME_VERSION=16.0 xcrun simctl boot "iPhone 14 Pro"
Setting a custom time for the Apple Watch simulator is not working.
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