Apple Watch Unlock Stopped Working

1P_Dave, you mentioned "Out of curiosity, does this happen when you wake the Mac from sleeping? If you leave the Mac running and prevent it from sleeping for 10-30 minutes then does Apple Watch unlock eventually start working again on it's own?"

This is exactly what happens with mine, except that in my case we're not talking putting the machine in sleep, but rather screen lock with display off, not full on sleep. (I have a MBP that is connected to power source pretty much 24/7). Scenario is always this:

When I go to sleep or go away from the computer for a night's sleep, the machine goes to display off (and locks the screen) after 30 minutes. When I wake up in the morning, I can 100% of the time (well with the exception when it once in a while asks for a password to enable Mac unlock with Apple Watch, but this is like once a week or so and I think normal behavior) unlock the Mac with the Apple Watch.

However, nearly 100% of the times after waking up from my sleep in the morning, I cannot unlock 1Password with Apple Watch (and when checking, Apple Watch unlock is not enabled in 1Password settings, but rather the Set Up Apple Watch button is showing). However, I don't need to enable or disable anything in the 1Password or Mac settings, but rather the 1Password unlock with Apple Watch starts automatically working after maybe 10-30 minutes, after the Mac has been unlocked with Apple Watch.

Interestingly, having the machine's display off with screen lock during the day, for shorter periods of time than a night's sleep, the Mac unlock with Apple Watch still continues to work normally, but ALSO, most of the time, not always though, 1Password unlock with Apple Watch works instantly after you have unlocked Mac with the Apple Watch. There's no 10-30 minutes delay like above.

This absolutely never happened with Monterey for me (I'm on 1Password 7 still). This started happening after upgrading to Ventura. Anyway, maybe a future macOS update fixes it for me, or maybe I need to do some of the troubleshooting mentioned earlier in the thread, but we'll see, I'll get to that when it starts bothering me enough.