MacBook Pro unable to communicate with Apple Watch Apple Watch won't unlock MacBook Pro

Up until yesterday, my MacBook Pro worked just fine with my Apple Watch - I walk up, touch the keyboard or trackpad, Mac unlocks and I get to work. No worries! Yesterday something changed and now my watch won’t unlock my laptop.

I’ve tried everything in the Apple Support post, including repairing my phone/watch, re-establishing two-factor authentication (2FA), and rebooting my laptop, iPhone, and watch. All to no avail. I tried the @Morwen suggestion with Messages because there was a gap in my message history, but that didn't do it.

When I try to enable my watch, I get the error message shown below (albeit after about 6 or 7 minutes later, not quickly like the gif image). My watch, iPhone, and MacBook are all signed in and communicating with Apple.



The only thing I can think of that might play into this is that I was setting up a personal VPN on my home router last night, but I’ve turned that off as part of my troubleshooting (and couldn’t replicate the issue).



Digging a little further, I found this message (repeatedly since yesterday) in my Console logs. It looks like I have two permissions conflicting, but I can't tell which is which, nor where to go to change one of them...                                                                                                                       


  Oct 21 02:17:54 Johns-MBP
  com.apple.preference.security.remoteservice[790]: objc[790]: Class
  AWDSecurityPrefAutoUnlockSetup is implemented in both
  /System/Library/PreferencePanes/Security.prefPane/Contents/XPCServices/com.apple.preference.security.remoteservice.xpc/Contents/MacOS/com.apple.preference.security.remoteservice
  (0x10d6018e0) and
  /System/Library/PreferencePanes/Security.prefPane/Contents/MacOS/Security
  (0x10fd0b210). One of the two will be used. Which one is undefined.




Environment includes:


2017 15" MacBook Pro with Mojave (updated) 
Apple Watch Series 3 with Cellular (updated)
I had a similar issue when I updated to Mojave.  These steps solved my problem:


Turn off bluetooth on the Mac
Open Finder and navigate to ~/Library/Preferences
Delete the file com.apple.bluetooth.plist
Turn bluetooth back on
If Allow your Apple Watch to unlock your Mac is off, check the box to turn it on
Test if your Watch unlocks the Mac