iMessage Sync Issues Post Sonoma 14.0 Update

It's not just you. Must be a Sonoma related issue - it started for me immediately after I upgraded.

With me, the problem manifests itself as delayed syncing, especially if my macBook was sleeping when the messages were received. In this situation messages that show up immediately on iOS or iPadOS can take up to 20 minutes to appear on macOS, and sometimes they just get lost entirely.

I don't know if this is the OP's issue but I did track down what was causing it for me. In my case I had purchased a new Macbook and messages wasn't syncing properly, especially when I was attempting to log into web pages that required a code sent my phone via SMS. I found the setting in my phone of all places, and not on my Macbook. In my iPhone I went to "Settings > Messages > Text Message Forwarding", and discovered that my shiny new Macbook was there but had not been enabled. I enabled it and restarted the phone for good measure, and that solved the issue for me.

I am having the same problem with Sonoma 14.0. My Mac Studio (M1 Ultra) and 5k 2019 iMac (also Sonoma 14.0) and syncing only sporadically with iMessage. Most messages do sync, but a bunch do NOT. Very random. Also iMessage on the mac constantly shows "syncing with iCloud" at the bottom. I've tried everything, from signing out of iCloud and restarting all devices. iPhone 14 pro max and 2020 iPad pro are syncing fine! Can we get another update. I have read about SOOOOO MANY people having this exact issue. Thank you!!!

Do not update to sonoma. If you want peace in life.

This must be a (synchronization) bug:

• Open (macOS, Sonoma) Settings, choose "Internet Accounts"
• Choose "iCloud" and click on "Show More Apps..." button
• Select "Messages in iCloud"
• The fourth control, "Status" shows "Not synced" and offers a "Sync Now" button
• Clicking on the "Sync Now" flashes "Syncing with iCloud"... then returns to "Not synced"
• ...even though all other internet functions work as expected — including sending messages from the macOS/Messages.app.

From the brief time my MBP tries to synchronize with iCloud, it should follow that either iCloud outright refuses syncing for macOS/Sonoma only and so is a server-side bug, or macOS (Sonoma, 14.4.1 in my case) has too short of an internal "timeout" setting.

As observed by others, Messages does synchronize eventually, and even interleaves the messages in a thread correctly, should I use macOS>Messages to send new messages.

➤ In fact, sometimes, the very action of sending a message via macOS/Messages.app triggers a (complete, properly interleaved) synchronization.

I solved my trouble with this but not sure if its related to the same trouble others are having...

I wrote yesterday about how I was having this sync issue but decided to format and install Sonoma 14.3.1 from scratch. I still was struggling to get things to sync from the Messages app on macOS in settings where you turn on iCloud sync and there is a button there to sync. Then later in macOS settings under iCloud and then "Messages in iCloud" I noticed this window I didn't see before. It showed a little window showing how many messages were in iCloud and a way to enable sync there and a sync button. So I clicked that then messages began to show up in my Messages app.

Ever since they began trying to make macOS look like iOS it's been such a mess with settings like this. Multiple settings or settings found in multiple places. You can't just go to one setting and have things change, you have to go all over or even on a different device or sign into iCloud on the web to finally have a setting change. Glad my trouble is fixed now but I wish things were not so confusing. I always knew to go to the app to turn on sync but now it's in both the app settings and macOS settings.

I am having exactly the same problem for a few months now ever since the Sonoma 14.1 update. I have tried every single workaround that has been mentioned over and over again and nothing has changed. I was hoping the update of 14.3.1 would fix this but it hasn't.

C'mon Apple this is the fundamental reason you push buying multiple devices so that every product syncs......but it doesn't!

Please fix asap!!

Same issues here. I've even tried reinstalling the OS. I've had a frustrating experience with senior advisors, too. When it comes time for a call back, I get an email claiming that they tried to call but couldn't reach me. Lame.

Check your Messages settings on your iPhone and let me know if you see something like this. This particular setting has the advisors stumped. The setting for my MacBook Pro also cannot be changed. It supposed to look like the settings for my MacBook Air and iPad (able to be toggled on or off).

Having the exact same issue. All was fine for about 24 hours, but now my MB Pro M1 16 running Sonoma 14.0 is not syncing. My iPhone 15, iPad Pro, and Apple Watch are all in sync... I've honestly had more "buggy" issues here lately with apple products, seems they might be rushing things to market.

My devices: iPhone 13 Pro Max iOS 17 and 3d Gen iPad Pro..11 inch.. both with the 17.4.1

iOS and a M1 Mac-mini with Sonoma 14.4.1. For quite a while I had similar sync issues and also

sync issues with deleting iMessages. Followed the above suggestions and this solved the issue. Actually

I turned the 'sync' between the iPhone and other devices "OFF' and then back 'ON' after a couple of

minutes. Now all syncing between the three devices, including the delete function. This 'fix' worked for

my devices. Current rewards do not guarantee future success!! Also very disappointed that APPLE has not

reached out with a fix for this issue. This time self help with community effort seems to be a partial fix but a real

fix should be forthcoming from the APPLE 'experts'!

Yes mine is like this too Jeep2691.

If you go to System Settings on your MacBook Pro > your name (Apple ID ) > iCloud > iCloud Drive > Apps syncing to iCloud Drive : you will see that you can switch Messages setting on/off.

Also when you get to iCloud setting you wills see a button saying 'Show More Apps". You can also turn Messages setting on/off.

Hope this helps . Oddly my sync problems have been okay the past few days. So far ...

I'm on 14.3.1 and still iMessage it not syncing with iCloud. Even if I go into iMessage settings on my Mac where it is checked and click on sync now, won't show what messages are on my iPhone. So many bugs in this OS it's driving me mad.

Just to add one more Apple Eco user to the mix with the exact same iMessage sync issues and attempted the same fixes with no change. Additional issue is that numerous incoming email messages from Apple Mail (me.com and cloud.com) to to the 'junk' folder....had nearly zero before. Also spent at least 20 hours with Apple tech, at the store, senior advisors and sent in numerous 'logs'.....received one call back from one senior in over a four month period with no fix in sight and still no fix in sight. I've been with Apple since about 2002, even worked part time at an Apple Store. Seems both the attention to detail and the followup are, sadly, going down hill. Maybe too much attention on the 'really' new stuff, Apple TV+ and who knows what 'advanced' projects as the bread and butter devices, software, upgrades etc are taking a really back burner for attention. This issue of iMessages is ALL OVER the net with the same lame answer to 'check you sync'...clearly many inputs are not ever read or misread. Really sad!!

I was having this same exact issue and on my mac I went to Messages -> settings and I clicked "sync across iCloud". I let that simmer for a bit and do it's thing, turned my phone off in the meantime. Turned my phone back on and all of a sudden all the new messages started showing up in both places. To see if it was a sync issue with cloud (and because it kept annoying me that it would show "syncing with iCloud" at the bottom of the messages box on my mac), I went back to the settings and unclicked sync and it still works.

Maybe try that? Good luck!

Syncing worked for me, too.

For those who find tech stuff maddening and unnatural, here are the steps:

1. Go to Settings in your phone
2. Tap on your name
3. Tap iCloud
4. Tap iCloud Drive
5. Tap Sync this IPhone and let it think for a minute until the green toggle is no longer grayed out.

That should fix it for some of us! Fingers crossed. I think it also took care of the Google calendar that wouldn't sync with my iPhone calendar.