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My Apple Watch 2 unlocks my Mac. But try as I may, I've never been able to get my Apple Watch 5 to do so.
 
That still didn’t work for me. Thanks though!
Maybe the fix listed here would work for you:
 
Thanks, just tried that and am still having no luck at all.
 
Maybe the fix listed here would work for you:
This procedure worked for me on two watches that would not unlock my MBP. They both now work perfectly every time.
 
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After roughly 15 min or so from doing the steps above, my MBP prompted me to setup my Apple Watch to unlock my Mac, and now everything is working as it should!
 
I was having the same issues .... watch and iMac and MBA all up to date but the unlock with watch stopped working. I noticed that the silent mode on my watch somehow had been activated ... when I deactivated it the watch is unlocking my machines again.
 
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