Is anyone having problems with synchronization of messages between their Apple Watch and iPhone? I think (not 100% certain) my problems pre-exist iOS 17.
My devices (iPhone, iPad) are on iOS 17, AW is on watchOS 10.
I’m observing a couple of problems.
If I initiate a new message on my AW, most times (but not every time) the message never delivers. It attempts for a while and eventually comes back with the “failed, retry” indicator. These are messages being sent to other iPhone users.
Similarly, my AW is often (but again, not always) out of date with messages that are sent to me.
This evening I experienced yet another oddity. I received a notification on my AW of a new message. I was able to read the full message in Notification Center on my watch. However, when I launched the Messages app on my AW, the message wasn’t there.
All of this activity is when my watch and my phone are on the same wifi network.
I haven’t tried to replicate the problem when I’m out with only my watch and connected via cellular. Not sure if that use case exhibits the same problem.
I’m at a loss on how to troubleshoot.
I’ve rebooted all devices of course. I reset network settings on iPhone (read that one somewhere as a possible cure). All the other settings are correct (signed in to iCloud, etc). This message synchronization has worked fine for years on older watches and the ultra.
Only thing I haven’t done is re-pair watch with the phone. I’ve been trying to avoid that punishment. 
Any thoughts on this one?
I have had this issue since the day I got my AW (I am still using the series 4). All devices are up to date from an OS perspective. It’s very rare when my Messages are in sync. Literally, maybe once every few months. I have this same problem across my Mac, iPad, iPhone. I’ve rebooted countless times, I’ve done all the things you mentioned. The one that gets me is my iPhone (always up to date) has no new messages. My iPads (Pro and Mini) consistently tell me I have anywhere from 5-10 messages unread still. The Mac message sync issue is mainly dealing with spam/junk texts, even though I delete on my iPhone, it doesn’t delete everywhere. Honestly, I kind of gave up on this part.
To add one more data point to this…
This morning I tried to send a message from my AW. As usual, it failed. This time, when I tapped retry I selected the “Send as SMS” option. Message was sent immediately.
Does this give anyone any indication of what my root cause may be?
FWIW, I re-paired my AW with my phone. Seemingly helped for a day. Alas, this morning, messages stopped synching with my watch again. I’m at a loss
One last bounce… any other ideas?
Are you using iCloud for Messages?
I have found that some sync problems can be forced to resolve by signing out of iCloud and signing back in. The sync becomes complex when there are multiple devices, and it’s possible that one device’s cache is messing up the others. You would think that the iPhone’s sync status would dictate the Apple Watch’s status, but clearly something else is happening. Signing out may or may not fix that, but it is something you can try yourself (before going to Apple’s tech support).
If you’ve got a Mac involved, I’d sign out on all devices and then sign in on the Mac. In the Mac’s Messages Preferences/Settings, there is a button that you can press to force a sync. If you force a sync, it should get all the up to date messages. (If it doesn’t, then you probably need to contact Apple to get them to fix the problem on their end).)
If the Mac is now up to date, then log into iCloud one at a time on each device, waiting for Messages to sync.
This is definitely a long shot, but I’ve seen it work for other weird sync problems.
After that, I suggest going to Apple tech support. They are the only ones with any hope of official understanding of just how and when the Apple Watch syncs its Messages app.
Thanks for the detailed suggestions. Yes, I use iCloud for messages across multiple devices. Will need to try your steps.
I am closing the loop on this in case someone else stumbles on this thread. The final resolution, thanks to Apple escalated support, was erasing watch entirely and restoring from backup. That has (finally) resolved the problem.
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Well, not the final resolution. The problem is recurring. Very frustrating as I never know when I can trust the AW to either be up to date with messages or successfully deliver a message.