This past weekend I had to unpair and re-pair my Apple Watch after the most recent WatchOS 7 and iOS 14 updates. Applications would neither install or update. I can only presume something was failing in the handshake or certificate management that iOS and watchOS use to ensure that the app is legitimately licensed for you on your device. Unfortunately the common wisdom seems to remain that the only sure way to resolve this is to un-pair and re-pair your watch. Apple needs to get their stuff together on this issue.

After this was completed I needed to re-enable the wonderful Apple Watch ability unlock your Mac. Unfortunately I was greeted repeatedly with the following dialog:

To allow your Apple Watch to unlock this Mac, your Apple Watch must be unlocked.

Unlock your Apple Watch and try again.

The problem is my iPhone was unlocked as was my Apple Watch. After multiple reboot attempts of macOS, watchOS and iOS I still remained stymied.

Fortunately someone on the apple discussion forums discovered a solution. Thank you to them for this.. The solution requires going into the macOS Keychain Access app and doing some cleanup as well as one of your user Library folders via macOS Finder. It would appear that, over time, redoing pairings can take a toll on the security stores for macOS, iOS and watchOS. When I went thru these steps I found keychain entries going back across all of my watchOS variants and computers I am no longer using. It’s definitely worth checking this out if you are a long time use of Apple Watch devices and/or use multiple macOS machines.

Disclaimer: Follow these steps at your own discretion. I cannot be held accountable if your computer refuses to boot afterward (tho I would find this outcome unlikely).

  1. Open “Keychain Access”
  2. In “View”, enable “Show Invisible Items”
  3. Search for “Auto Unlock”
  4. You should see a whole bunch of application passwords for “Auto Unlock: XXXX’s …”
  5. Select all records and delete (this will reset/disable auto unlock on other Macs if you use multiple Macs)
  6. Whilst still in “Keychain Access”, search for “AutoUnlock” (no space)
  7. There should be 4 entries for “tlk” “tlk-nonsync” “classA” “classC”
  8. Select 4 records and delete (don’t worry if they re-appear, the system repairs this automatically)
  9. Open “Finder” and navigate to “~/Library/Sharing/AutoUnlock”
  10. There should be two files “ltk.plist” and “pairing-records.plist”
  11. Delete both files
  12. Open “System Preferences” and try enabling auto unlock. You may need to enable it twice, the first attempt will fail.

In my case where I was seeing the activation of this feature take as much as 1 minute I know am able to connect my Mac laptop and desktop machines in about 5 seconds.

I hope you fare as well.

UPDATE: If you find these steps still don’t work there is one other set of steps you can use in addition to these. It will force a reset of Bluetooth Profiles for all connected apple devices, so be sure if you are using a Bluetooth keyboard to plug it into your computer first with it’s USB cable.

  • Plug in a hard-wired (Non Bluetooth) keyboard and mouse. You can use the charging cable for the devices and plug them into the mac – it work the same. For the Apple Magic Mouse since you have to have it plugged in underneath the mouse you should find an old USB-plugged in
  • Option-Shift-Click Bluetooth icon in menu bar
  • Select Debug
  • Select Factory reset all connected Apple devices.
  • Restart your machine.
  • Return to “Security and Privacy” in Settings and checkmark “Use your Apple Watch to unlock…” again. You might need to repeat this one or two times.

Seriously Apple.. you need to fix your stuff.