Unlock with Apple Watch not working...

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EDIT: Jake has solved the mystery for me (see posts below). Thanks!

This is my first time trying to use this feature, and it's not working. This is my new 2019 iMac and I'm on macOS 10.15.5 and watchOS 6.2.5. In System Preferences > Security & Privacy I have "Use your Apple Watch to unlock apps and your Mac" selected. Two-Factor Authentication is on for my Apple ID.

So, say I now go to System Preferences > Security & Privacy again and click the lock icon on the bottom left. Immediately I get a notification on my Apple Watch prompting me to double-click (the digital crown) to approve. However, when I do so, nothing happens. The window that says "System Preferences is trying to unlock Security & Privacy preferences" doesn't go away, and I am forced to click the Use Password button.

So I tried restarting both my Mac and Apple Watch. When I got the login screen, it said I had to enter my password to enable unlock with Apple Watch after restarting. So I did so. However, when I tried to unlock the Security & Privacy preferences again, it still didn't work. Also, I tried logging out and then logging back in again, and there is not even an option to log in using the Apple Watch. I also tried disabling and re-enabling the "Use your Apple Watch to unlock apps and your Mac" option but that didn't fix it either.

What gives?

EDIT: I discovered my Apple Watch DOES automatically unlock the iMac when resuming from display sleep or screen saver, but it's still not working to approve within apps and also not working when logging on.
 
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I think it is not the digital crown, but the side button that needs to be clicked to authorize things. I just tested on my watch and it worked that way.
 
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usagora
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I think it is not the digital crown, but the side button that needs to be clicked to authorize things. I just tested on my watch and it worked that way.

*facepalm*

I'm sure you're right. I guess I rarely use that button, so since the digital crown is so prominent, I just assumed that's what the prompt was referring to. Will try when I get home. Thanks!
 
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Jonathan, been there, done that! Apple has actually added a visual prompt on the Watch to point to where to press, so I guess they got a lot of calls about this one.
 
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But...that still doesn't answer why I'm not able to unlock with my watch when logging in. I understand that I have to use my password after restarting (just like with iOS with FaceID or TouchID), but if I log out, then click my user account to log back in, there's no option but to enter my password. Not a huge deal, but if it's supposed to let me unlock with the watch, I'd like to know why it's not giving me that option in that situation.

Jonathan, been there, done that! Apple has actually added a visual prompt on the Watch to point to where to press, so I guess they got a lot of calls about this one.

Yes, it was pointing, but I just assumed it was referring to the right side of the watch in a general sense, and, again, there's the crown sticking out, so I pressed it. LOL. Thanks again.
 
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Yep, that is how it is designed. If you log out, there is no further link between the account and the watch, so you have to log in again. Once logged in, the link with watch/phone/mac is established and as long as you stay logged in, the watch can unlock the Mac for you. But log out, or reboot, or shut down and restart, and that link is destroyed for security so you have to reestablish it. When you provide the password, you are demonstrating that you (and therefore the watch you are wearing) are authorized to open the account. But if you log out the account on the Mac is closed and the authority of the watch is canceled. When you return, you have to prove again you (and your watch) have the authority to access the account. Stay logged in and the connection of watch and account is preserved.

Now you could make a case that as long as you are in constant contact with the watch, and it has its own security, the Mac should just accept that any time you get close it should allow the account, but that is not how Apple designed it. They put in more security, I guess because they feared that it's easier to crack a Watch password than a stronger password on a Mac. Apple is security paranoid, which is not always a bad thing...
 
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Thanks, Jake. That makes sense. I just didn't realize that's how they designed it, so I wanted to be sure I wasn't missing something.
 
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I have read this post with interest and it certainly has helped as I could not understand why I could not use my Apple Watch to log into my Mac, so thanks. However, when I go to System Preferences > Security & Privacy and click the lock icon on the bottom left, Immediately I get a notification on my Apple Watch prompting me to double-click to approve and on doing this it works, fine, but when I put the Mac into sleep mode and then try to “wake” it up it does not work so I have to enter my password again. Perhaps I am missing a point and if this could be explained I shall certainly appreciate it.
Thanks
 
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There was a bug in watchOS 7 that caused some issues with the unlock of Mac function. There is an update to watchOS version 7.1 that addresses that failure.

That said, @Alphalogan, to activate the  Watch unlock function, after you click on the Lock icon and provide an Admin password, you have to then click on the "User your Apple Watch to unlock apps and your Mac" box and then click the lock icon again to close it. Then the Mac, your iPhone and the  Watch need to be connected both by Bluetooth and on the same WiFi network for the function to work.

Screen Shot 2020-11-09 at 11.43.17 AM.png
 

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