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

Update: this resolved for me with iOS 17.4.1. Since I had the problem both before and after installing iOS 17.4, I'd assumed the cause was the change to Sonoma 14.4, but I've now seen posts about it happening with other combinations of MacOS and iOS, so I guess it's just a tricky thing for Apple to solve for all cases.

Found this thread through some googling, attempted the Sync Now solution, but didn't have success.

However, I believe I found the culprit for me: My phone is lying about how much storage space is actually available.

Context: I pay for the 2gb iCloud storage space, and it's quite full, but my phone has only a 256gb storage space. When I look under Settings -> General -> iPhone Storage, it says only 96gb is being used, but I've tested this in the past and it is not true; trying to install certain games that require storage space and getting error messages about storage space being full (even though 96gb/256gb), then removing items stored on the phone made those error messages go away.

So, steps to my solution:

1. (most important step!) Delete some items permanently (such as things waiting in Deleted in Photos, etc)
2. Sync on Macbook (follow steps by urmi02 Messages between Mac & iPhone not syn… - Apple Community)
3. Sync on iPhone
4. No more inconsistencies between iPhone and Macbook pro!

Hope this helps anyone else.

Apple doesn't play well with VPNs. I usually have one on all the time. After the last update iMessage didn't sync between mac and phone. Turned off the VPN and all synced perfectly. Not an ideal solution. Get it together Apple.

After doing "Sync Now" from iPhone 11 (iOS 17.6.1), the iMessages on my MacBook Pro 2023 (Sonoma 14.6.1) still didn't sync. In addition, I went to MacBook Pro->Messages->Settings->iMessage->Sync Now. This finally synced messages from iPhone to MacBook Pro.

What appears to have happened on my device is that on iphone settings > messages > send & receive, somehow I was no longer connected with my apple ID because it gave me an option to send messages via my apple ID. (it was only sending as my phone number).

So I went ahead and tapped to link with my apple ID. It did nothing, so I pressed it 3 more times. It finally then registered to link to apple ID and I got the normal apple security hoops to jump, after which I was then able to send, receive, reply from, and start new conversations from either my phone # or my apple ID email.

So now things look like they are working *somewhat* better. Sent a message from mac messages app to another iphone user, sent fine and was delivered.

However when I texted from my mac a Google Voice number that I also own, it was received immediately on GV online, but on my mac it stalls then says not delivered, which is not true actually: it was delivered. I replied from GV online and all this tracked fine on my iphone, but mac never got the reply message, in fact it still says my test outgoing message never delivered. So I'm partway there.

I had this problem, and I think I found a fix. In the Messages app on your Mac, go to Settings>iMessage>deselect "Enable Messages in Cloud."

I don't know if it's the same with you, but I think my issue was that my iCloud is full, so nothing was syncing. After I deselected "Enable Messages in Cloud," everything (eventually) synced in the app on my Mac.

Hope this helps!

Indeed. And this is the same now on Mac OS Sequoia 15.0.1 and IOS 18.0.1

Same issue with support : they were friendly but came with useless things like sign/unsign, stop message forward, enable again.

Crazy that the biggest company in the world cannot have simple message synching mechanism working. Never had issues with Signal or Whatsapp ...

Working turnaround is reboot of the Mac, so now I reboot few times a week. A Mac. Reboot a few times a week to fix a bug. Something is wrong in Apple QA process. Times are changing :-/

I finally upgraded my MacBook Pro from Monterey to Sonoma 14.4.1 a week ago (May 8, 2024) and have experienced this behavior of messages not syncing with my iPhone 13 (running 17.4.1) enough times that I felt the need to check the Apple Community for help. Probably 80% of my texting is done from my iPhone, but on occasions when I open my laptop to respond to a GREEN text message string that appeared on my iPhone, it was not on my laptop. This problem seems to occur mostly with GREEN text messages, although I have also experienced a delayed sync with BLUE iMessages. Prior to Sonoma 14.4.1, all messages synced seamlessly. As others have mentioned, my only resolution has also been restarting my Mac when this happens...which is a major pain. Just wanted to throw in my 2 cents with hopes that Apple will address this obvious BUG with Sonoma 14.4.1...PLEASE AND THANK YOU.

marcfromcasteau, that's brilliant -- switching my Mac's wifi off and on worked for me, too. Still will have to do it regularly, when it shouldn't be necessary, but at least it's much easier than iCloud syncing. Thanks so much for discovering this.

UPDATE: Since my previous post on 5/15/24, I have updated my macOS to Sonoma 14.5, and my iPhone 13 Pro Max to iOS 17.5.1. I was hopeful these updates would address the problem we all are having, but unfortunately no luck. This problem appears to primarily occur for me with the SMS green text messages not syncing between my iPhone and my MacBook Pro. Previously I felt that restarting was the solution, but even that is not working consistently. Before restarting both my iPhone and Mac, I close both out of Messages. Then restart both devices as close to simultaneously as I can, then open Messages about the same time on both, hoping they are both pulling down the same data from iCloud. However, some SMS messages displayed on my iPhone do not pull down to my Mac from iCloud. Eventually (like days later) they can show up. But as I write this, I have a SMS message on my iPhone that I received 12 hours ago, and it still is not displaying on my Mac...and this is despite my restart routine of both devices. I did not have this problem before I upgraded from Monterey to Sonoma 14.4.1. And the issue appears to occur with SMS messages received on my iPhone that do not simultaneously display on my Mac. If I have my Mac open and receive a SMS message, it displays on both my Mac and my iPhone simultaneously.

PLEASE APPLE!!!! LOOK INTO THIS!!!! I used to troubleshoot software so I've tried everything I can think of, and you have a lot of user info/troubleshooting provided to you in this forum to assist you in fixing this issue!!

I have messages from one contact that show up on my MacBook Pro M1 Mx (Sonoma 16.6.1) and iPad Pro M1 (17.6.1) but not on my iPhone 15 Pro Max (17.61) - even though I am the texting the contact most days.

On my iPad, I tried pinning the iPhone missing contact and . . . magically the contact (and his messages) appeared as a pinned contact on my iPhone . . . but, when I unpinned the contact my iPad, they disappeared from my iPhone !

This outcome is is superbly repeatable !

In response to yoichi.takayama on 9/10/24, in my opinion, the reason you should sync iPhone first is that messages appear as they should on iPhone; you would not want to first sync your Mac messages to iCloud, since there are missing messages on your Mac. The goal is for Mac to pull down the complete messages that your iPhone synced to iCloud first. That being said, I still have a problem with SMS (green) text messages that sync from iPhone to Mac, but not in the same order as they appear on the iPhone.

The point of this entire issue is the fact that messages were syncing seamlessly between iPhone and Mac prior to Sonoma 14.4, and then stopped. Users now have to intervene manually by going through extra steps to try to get messages to sync between iPhone and Mac. Even after doing that, Mac may pull down a previously missing message string that iPhone synced to iCloud, but the message string does not appear on Mac in the same order that it appears on iPhone. We are now at Sonoma 14.6.1. Users have been posting on this bug since March 2024; it is now September 2024 and Apple has yet to address our concerns. Surely Apple employees have also experienced this problem?

This finally really helped by me.

I don't understand why, I have a blarge free space on iCloud, and pretty nice remaining space on iPhone, but after deleteing all deleted photos, and going through the steps (sync iPhone and sync MacBook) all finally synchronised.

Thank You!

I was having the same issue of messages (both iMessage and SMS) not synching on my MacBook Air compared to my iPhone, so I updated to the latest software (iPhone to 17.5.1 and MacBook Air to macOS Sonoma 14.5), and I'm still having this issue!

Only temporary solution that seems to work is signing out of my iMessage Apple ID, but that's a pain.

Has anyone found a solution? I never had "Enable messages in iCloud" turned on before this and never had an issue because you don't need that turned on in order for your messages to be synched up, that's just to keep them in the cloud for backups.

This finally really helped by me.

I don't understand why, I have a blarge free space on iCloud, and pretty nice remaining space on iPhone, but after deleteing all deleted photos, and going through the steps (sync iPhone and sync MacBook) all finally synchronised.

Thank You!