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

In my case ExpressVPN on my Mac seems to be the issue. When express VPN is on, my Mac doesn't get SMSs from my iPhone even after forcing a sync. Turn VPN off and force a sync and the missing messages are synced. Running Mac OS 15.0.1 and iOS 18.0.1

Here's what's been working for me:

• On your iPhone, go to Settings -> <your icon at the top> -> iCloud -> Show All -> Messages in iCloud -> Sync Now
• (Once it's done syncing, note how many messages it says are in iCloud.)
• On your Mac, go to System Settings -> <your icon at the top> -> iCloud -> Show More Apps -> Messages in iCloud -> Sync Now
• If your MacBook still shows messages that your iPhone doesn't, you may need to repeat the steps one more time. The message counts the two devices think are in iCloud should match by the end. I still have one or two messages on my phone that never reached my Mac (or iCloud, presumably), but everything else shows up for me on both devices and the counts agree.

Doing this, sometimes multiple times a day, is a pain, as is unknowingly missing messages, so I hope Apple fixes the problem soon.

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.

Discovered a relatively easy work-around. Here is the scenario :

Mac OS Sequoia 15.0.1 and IOS 18.0.1

had few message away from home on the Iphone

Back home, open up the Mac and - of course - nothing happens on it. No synching.

Somehow decided to simply turn-off the wifi on the Macbook. Waited 30 secs or so.

Turned on the Wifi and - bing - instantaneously all messages from the day started to pop up on the Macbook. Yeah !

To be complete, Bluetooth remained on - only Wifi on the Mac was turned off and on ; Iphone was connected on Wifi, bluetooth on.

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 !

urmi02 previously stated (see below) that they submitted a Bug Report to Apple, suggesting others do the same. I followed suit and submitted my Bug Report on July 19. I urge everyone to take the time, since Apple is ignoring us.