Check out this thread on fixing Apple Watch unlocking Mac
https://discussions.apple.com/thread/251803595?answerId=253458029022#253458029022
Then follow with this thread
https://discussions.apple.com/thread/251826134?answerId=253504359022#253504359022
I also found that it took awhile for the iCloud Keychain records to propagate and merge on all the systems. More so when you have multiple devices sharing the keychain (I have 4 Macs, the iPhone, and the Apple Watch). I followed both of the above threads, but it was not reliably working until the next day, when I tried again. And I did have to click the enable check box twice the next day, but then it stuck.