I updated my AW7 to WatchOS 10.1.1 on Tuesday, ever since then silent mode for Messages doesn't work intermittently. I have checked that silent mode is turned on in the command centre, in the Watch app on my phone, and I've also restarted the phone - same results. I had a chat with Apple Support but they weren't able to offer any solution other than to un-pair / re-pair, which in my mind is the nuclear option and I will only do that as a last resort.
It's intermittent, which makes it even tougher to troubleshoot.
I've also noticed this occur once on my iPhone since the update to iOS 17.1.1 as well.
Is anyone else experiencing this issue?