Messages between Mac & iPhone not syncing after upgrade to MacOS Sonoma 14.4 & iOS 17.4

I meant to add . . . though the missing contact appears on the iPhone when pinned on the Mac, the messages the pinned contact contains are not up to date . . in fact the last one is 2018, despite the messages on the Mac continuing up to now (Sep 2024) at the time of writing !

This issue has gotten even worse since I first posted about this in the spring. Manually syncing does not help. And now my Mac is creating separate group chats depending on where I reply, specifically with non-iMessage group chats. What do we have to do to get Apple to at least acknowledge this issue?

I know Apple's marketing department swears that it's a new gizmo or feature that's going to sell people. But if you'd just get a reputation for rock-solid sync'ing across devices without all this goofy shutting off, re-syncing, manual syncing, etc. I think it would have more of an impact.

What's the point of staying in the Apple OS ecosystem if the sync isn't seamless?

Having ALL the same issues as everyone else. It's intolerable. Maddening. I'll miss a text because I'm not on my phone but I'm sitting right at my MacBook.

Hello again. Firstly I want to note that none of the solutions proposed in this thread have worked for me regarding the messages sync issue described below. 

Secondly, as I have posted several updates about my messages sync issue, I wanted to bring all my findings (including new information) into in one place. Here we go:

On my MacBook Pro M1Max [MacOS Sonoma 14.7] and iPad Pro M1 [iPadOS 17 and, since Monday, iPadOS 18], I have a contact whose messages are up to date - many messages between us this month and loads more going all the way back back to July 2009.

On my iPhone 15 Pro Max [iOS 17 and, since Monday, iOS 18], I can scroll and find this contact but the last visible message is March 4th 2018! That is, all our messaging since then does not appear on my iPhone (but does on my Mac and iPad!)

This is the only contact manifesting this problem on my iPhone. 

Pinning the problem contact on my iPhone works but does not update his messages which still end at March 4th 2018. 

Same issue here, I called Apple Support and they basically shrugged their shoulders and said sorry. Neither SMS nor iMessage sync properly - they will only sync if the messages were sent when both my iPhone and Mac were on and running at the same time. Apple, this is abysmal. Many of us pay extra for iCloud storage to keep our messages in the cloud and synced across devices, and you are not providing what we are paying you for. Why has this gone on so long without even being addressed?

Same issue here, I called Apple Support and they basically shrugged their shoulders and said sorry. Neither SMS nor iMessage sync properly - they will only sync if the messages were sent when both my iPhone and Mac were on and running at the same time. Apple, this is abysmal. Many of us pay extra for iCloud storage to keep our messages in the cloud and synced across devices, and you are not providing what we are paying you for. Why has this gone on so long without even being addressed?

Same here with Mac OS 15 and iOS 18. Also with Notes. Happens to my wife too. Ironic that google docs syncs instantly with iOS and MacOS. They do a better job on the Apple platform than Apple does. Has to be the iCloud server that is the problem.

Something I just discovered that I never noticed previously...when I did a SYNC NOW of my messages from my iPhone 13 Pro Max running iOS 18, with my MacBook Pro running Sonoma 14.7, the timestamps were different. This was VERY important to me, because I think of my daughter every year at the minute she was born at 9:51 PM. When she can't take a picture (because she's sleeping), I just send a text at 9:51 PM, so she will see I was thinking of her. I am providing screenshots (below) of the text string comparing my iPhone and MBP messages timestamps after syncing. Note the timestamp differences!!

iPhone MacBook Pro

7:39 AM 7:46 AM

1:03 PM 1:23 PM

5:09 PM 5:12 PM

9:51 PM 10:03 PM

APPLE COME ON!!!!!!! PLEASE???!!!!! Why are you not taking us seriously? Why do you expect us to put up with this?

(And I thank the user marcfromcasteau who recently posted that the syncing problem still continues after updating from Sonoma to Sequoia. I was thinking of updating only to see if it took care of the problem, which apparently it hasn't.)

I had this problem last year and was able to fix it by calling apple care, it was just a box we had to check but it was so simple we both totally overlooked it and I can't remember how we got to the check box. I'll try apple care again and update. It had something to do with an iCloud setting.

Did anyone ever find a fix for this?

I am having the exact same situation. Did you ever get a solution?

Updated to Sonoma 14.5. Had the same problem before update and still have same problem after update. FIX THIS PLEASE APPLE ----NOW

Have the same issue, latest iOS (iPhone 14 Pro Max) and macOS versions (M1 Pro).

That worked for me! Don't know how my iMessages became unsynced. Thanks!

I'm having the same problem with my iPhone 13 Pro Max and my MacBook Pro updated to Sonoma. THEY ARE NOT SYNCING! Why has this problem persisted?