Same issue. This is frustrating, as I see no official statements from Apple this is not supported. The iPhone and Watch simulators are paired, but no iCloud on Watch. I tried everything, and I guess I have to start using physical devices. Very disappointing.
fourthopinion
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Has anything changed, or is CloudKit still being blocked on watchOS simulators at this point? (I'm new to iOS/watchOS development but the lack of clarity and plethora of bugs has not been a nice experience coming from Dart/Flutter environment.)