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I've been having this too, since the watchOS 10 upgrade. (I skipped 10.0 and went straight to 10.1.) Seems intermittent but really annoying when it does happen. I've been able to "fix" it (for a while) by going to Settings → Messages on my phone, going to Notifications, and toggling it off and back on again.

I know my watch "knows" about the messages that come in even when the notification doesn't pop up. If I open the Messages app, they are right there, with the little unread blue dot.

Hoping 10.2 fixes it, supposed to be released sometime next week. I really should wait longer before doing these major OS upgrades.
 
What annoys me is the on again off again Apple Watch unlocking my Mac Studio. It will work without a problem for several days, than it will stop doing it. I don't have clue why it stops. I go in and re-do the authorization and it starts working for awhile. But if I just knew the reason I would stop doing what it is that is causing it.
 
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Honestly there are so many little buggy things about the watch, i cant keep track of them all. The stocks app doesn’t update, the unlock Mac works then doesn’t, and among the biggest hassle of them all is the messages being unable to send, and not getting notifications. I say all this as someone who still appreciates the device and its usefulness, but man there are a lot of bugs in it.
 
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Many times when I get an iMessage my iPhone 15 pro or Apple Watch series 9 will not notify me but it will go through on my 2020 iPad Pro. All are on the latest OS.
 
Missing message notifications is becoming increasingly troublesome. I'm missing some time-sensitive texts. I upgraded to the watchOS 10.2 RC (+ iOS 17.2 RC). Will see if it keeps happening or not, while it seems good at the moment I feel like I won't "know for sure" until I've been running for a few days without issue.
 
I have an app called Quakefeed. It is a primo Earthquake notification app. Most of the time what pops up in the iPhone viderates me on the AW, But no always. I have the app on the iPhone set for 5m and up except for the local area which I have set for 3m and up. Yet I continue to get notifications of the AW of less than 5m from everywhere. World wide there are a lot of 4 to 4.8m earthquakes.
 
Missing message notifications is becoming increasingly troublesome. I'm missing some time-sensitive texts. I upgraded to the watchOS 10.2 RC (+ iOS 17.2 RC). Will see if it keeps happening or not, while it seems good at the moment I feel like I won't "know for sure" until I've been running for a few days without issue.
I wonder if it is the app, and not the OS. We might be blaming the wrong side of the issue.
 
I haven't received reliable Message notifications for months. It was happening for me before watchOS 10. I've tried most of the fixes I've seen online but nothing has worked long-term.
 
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I know this is an old thread, but I just solved this notification issue with my Apple Watch. The macOS Messages app was interfering with notifications (hijacking the notification lol?), causing them to appear silently on my iPhone and watch.

To fix it, I logged out of iCloud in the macOS Messages app, and now notifications are working properly on my watch. Not a perfect solution but fine for me.
 
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