This is a problem I have but I have noticed a potential connection issue with iCloud which I think might be causing the problem. Here is my description:
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I have a frustrating problem with unlocking my Macs with Apple Watches. If I restart and log in to my computer then lock it my Apple Watch unlocks it reliably and consistently every time I try. As soon as I log another user into the computer Apple Watch unlock no longer works either for the new user or the original logged in user, even if one of them is logged out again. The only thing that gets the unlock working again is a re-start and sometimes that does not work for some time after the restart.
One other thing I have noticed is that when the watch unlock is working I am able to see my iPhone's personal hotspot in the list of available WiFi but when the watch unlock breaks (ie when I log in another user) the hotspot disappears. I suspect the whole issue may be related to the machine using it's connection to iCloud perhaps?
This behaviour is the same on an iMac and a Macbook Air both updated to the current operating system release and one of which has a completely fresh install of highSierra. Both phones (6s / 7) and watches (2 original sports and 1 original stainless) are running the latest releases of their respective operating systems but it is worth noting that this behaviour has always been present in previous versions and I was hoping the latest releases would fix it.