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I've been using Watch unlock quite happily, including for sudo. However, it stopped working recently.

  • Today, I noticed the Security & Privacy pane setting "Allow this mac to be unlocked with Apple Watch" unexpectedly unchecked.

  • I tried to check it again, and was met with an error, [Apple ID not signed in]. All the other Apple ID linked services were still available and active, including for example active syncing of Notes.

  • In the iCloud pane of System Preferences, I logged out and logged back in, but now the unlock with Watch checkbox no longer appears at all.

Can I re-enable watch unlock, or has Apple regressed this feature on Monterey?

(In re-authorizing & re-syncing iCloud, I'm a little disappointed to be asked for my phone lock pin on my Mac, instead of authorizing it from my phone. Bad training for users. Oh well.)

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Sign in with Watch has reappeared. It seems to have been an issue with iCloud partial sign-out or partial sign-in. Component services of iCloud seem to authorize separately, take time to sync, and finish syncing at different times. I got unlucky, (impatiently) observing the intermediate state.

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