Messages not syncing on my 2019 iMac after upgrading to Ventura

[usagora]

Just as the title says. On my way home from work, someone replied to a Messages conversation (saw the notification on my iPhone), however, when I opened Messages on my iMac (now running macOS 13.0), their "like" and response were not there. I remoted into my M1 Mini at work (also running macOS 13.0), and her like/response DID show up there. What gives??? I've already tried signing in/out of Messages and the "Sync Now" button, but to no avail.

UPDATE: So I just replied to her message from my iPhone, and my reply shows up in Messages on my iMac, but her message that I was replying too still doesn't show (it's like there's a "hole" in the conversation now)

 

[toronado455]

2018 Mac mini same problem after upgrading to Ventura. Conversations I delete on my iPad are not getting deleted on Messages on the Mac. Also tried the "Sync now" button to no avail.

 

[usagora]

2018 Mac mini same problem after upgrading to Ventura. Conversations I delete on my iPad are not getting deleted on Messages on the Mac. Also tried the "Sync now" button to no avail.

Well, a few days ago I went back to the conversation in Messages on my iMac to download a picture she had sent (having forgotten about the issue I had), and noticed there was now a "blank page" image shown where the picture should've been--can't download the picture, so I did it from my iPhone instead. Just looked back now after reading your post and noticed all appears normal now in the conversation on my iMac--as if nothing had ever happened. All files/messages/likes show up. So strange, but hopefully just a fluke.

Haven't had issues with deleted messages syncing, but last time I did, for some reason I discovered that Messages was disabled in my iCloud settings on my iPhone, so you might want to check on that. Settings > Apple ID > iCloud > Show All > Messages

 

[toronado455]

I don't have a "Show All" step on my iPad or iPhone. But my iPhone and iPad are syncing properly with each other. It's only my Mac that isn't syncing.

 

[usagora]

I don't have a "Show All" step on my iPad or iPhone. But my iPhone and iPad are syncing properly with each other. It's only my Mac that isn't syncing.

You said, "Conversations I delete on my iPad are not getting deleted on Messages on the Mac." That was exactly the problem with my iPhone I was having that the steps I outlined above fixed. I would delete a conversation on my iPhone but it would still be on Messages on my Mac.

Not sure why you don't see the "Show All" on your iPhone. Which iOS version are you on? I'm on 16.1, but this has been there before 16 as well:

Settings > Apple ID > iCloud gets me to this screen (you can see "Show All" about halfway down):

Then clicking "Show All" gets me to this screen:

Then tapping on Messages gets me to this screen:

So you need to be sure "Sync this iPhone" is activated.

 

[toronado455]

Thanks for the screen grabs. I have iPad iOS 15.6.1 wherein all apps that use iCloud are shown by default (so no "show all"). But Messages is activated in that menu on both my iPad and iPhone. So that doesn't seem to be the issue.

I'm downloading iPad iOS 16 now. Maybe the iOS software update will fix things.

(My iPhone is also on iOS 15.6.1 so after updating the iPad, I'll update my iPhone next.)

 

[toronado455]

Got iOS 16 installed on iPad and sync with Mac is working again! 🎉🎆🎇

Tested recovering conversations from the "Recently Deleted" and it syncs with the Mac perfectly as well. Not sure if "Recently Deleted" is new for iOS 16, or if I just never noticed/used that before.

 

[Nihilus]

Glad to see I'm not the only one. I've got a 2020 M1 Air. Worked fine before the update. After the update it's hit and miss. All the settings on the computer and phone are correct, and I still get messages coming through and sending fine on my work laptop that's still on Monterey. iPhone is on 16.1.1.

 

[Zrealtor]

I have been with apple support ongoing for three days with no resolution. All my systems sync messages with the exception of MacBook Pro 2019 on Ventura. Even my old mini macs are working like a charm with the old OS. frustrating that this is an issue…