Messages deleted on my Mac are not deleted on my iphone

I went through nearly a month of back and forth with Apple Support with no resolution. I was running iOS 16 on my phone and Monterey on my iMac. Their final word was that they were aware of the issue and it would be addressed in a future release. Apparently that release was Ventura. As soon as I updated my iMac the issue resolved.

My previous post was removed, so let me rephrase it, stating THE FACTS ONLY

1. Apple Support didn't help me to resolve the issue. They asked me to sign out and back in to AppleID on my iPhone which caused unexpected difficulties, and I strongly advise not to do that if you don't have to - this solution from Apple Support didn't solve the problem but it caused additional problems. In case you are interested - let me know and I will elaborate.
2. Upgrade to macOS Ventura resolved the issue. I don't want to break any community rules here, so I will not speculate. What I can share though, is based on my own programming experience: various IT companies create different APIs and sometimes you need to upgrade both sides of communication at once (for example iPhone and mac), otherwise some functionalities will stop working. Was it the case with you, or did you upgrade iPhone first and then mac, after few days? Did it start working after upgrading to Ventura? For me yes.
3. Why did Support come up with a solution that didn't resolve the problem? I don't know, again I don't want to guess.

Try going to System Preferences/iApple ID/iCloud and stop Messages syncing by unchecking the box. Wait a couple of minutes, then check syncing. 

Hey there mattkis,

Thanks for reaching out to the Apple Support Communities. Based on the information you've provided, we'd recommend reaching out to Apple Support directly from this link here: Get Support - Apple

They'll be the best option to work with you closer on this issue.

Take care!

I have an iMac 24" ,with an Apple M1 chip running MacOS Monterey v.12.6. I also have aniPhone 14 Pro Max running iOS 16.0.3, an iPad Pro 12.9" running iPadOS 15.7, an iPad Min Generation running iPadOS 15.7 and an Apple Watch Series 8 running WatchOS v.9.0.2. All of the devices are connected to the same Apple ID and all are configured to sync messages across devices via the iCloud.

The problem is they don't sync messages across the iCloud. The issue seems to have started when I got my iPhone 14 Pro. Messages deleted from my phone seem to be deleted everywhere. Messages deleted from my iMac are deleted from my iPads but not my iPhone. The reverse is true, messages deleted from ,y iPads are deleted from my iMac but not my iPhone. Messages deleted from my iPhone are not deleted from my Apple Watch.

I have been trying to work with Apple Support for a month, up to and including having the issue sent to "The Engineers". The engineers requested screen shots and videos of the problems and the ability to install log recording capabilities in order to record logs from my phone and iMac. All requests were granted and the material sent to Apple 2 weeks ago.

2 emails to the support rep who had "taken ownership" of the issue went unreturned. I called Apple again today and got a new rep, who couldn't understand why Rep 1 had not gotten back to me. She then assured me that she had "taken ownership". she then asked me to verify that all devices were up to date. When I said the iPhone was running 16.0.2 she refused to go further until it was up to date. (There is nothing in 16.0.3 related to the problem, and it persists.)

Once the phone had been updated she then said "We're aware of the issue and it will be addressed in a future update." That was it. She was finished. She stopped just short of saying "Is there anything else I can help you with?"

I'm running iOS 16.1 on iPhone XS and iPad Air. I run Monterey on an iMac and a MacAir.

If I delete an iMessage conversation on the iPhone it goes and deletes it from both the desktop and laptop (and iPad).

BUT... if I delete a conversation from either the MacAir or the iMac, the item is delete from the other computer but NOT the iPhone or iPad.

It looks like this is known issue and I hope it is fixed because my old iMac cannot upgrade to Ventura. The laptop can, but I alway wait for the "point 1" release of a new Apple system (because I've been a software programmer for 40 years... and I know the old riddle well:

Q: How can you tell who the pioneers in software are?

A: They are the guys and gals with the arrows in their backs!

If this gets fixed, please post about it here as a lot of us probably "follow" this discussion.

I am leading a group of software programmers and I tell you: don't count on it, Apple will not resolve the issue with Monterey. They don't say a word, but it looks like there's new API endpoint used in Ventura. The same was some years ago, when Notes stopped syncing. Very big issue for me is, that the Apple Support doesn't know this. I personally spent an hour on the call and the only thing they suggested was logging out and in again, which obviously didn't work. Not sure why they suggest not working solutions. Also, it cause additional issues, as I lost all my cards in Wallet, and it turned out when I was standing in front of the goods that I bought, without any way to pay. That's a situation. So I don't recommend logging out and back in, as it has unexpected results.

I have the same exact problem after purchasing my new iPhone 14. iOS 16,0.2

Messages deleted on MacBook DO NO DELETE on iPhone. Messages deleted on iPhone DO DELETE on MacBook. Major hassle that devices do not sync.

I've also tried signing out of icloud and that doesn't help. Note that I am signed into icloud on all devices with my same apple id.

MacBook Air M1 2020, MacOS 12.6 and iPhone 14. iOS 16,0.2

Just spend 40 minutes on a chat about this very issue. A lot of screenshots, resetting Mac and iPhone and signing off from both and signing back on to eliminate the obvious, and no results. I had to end the chat as I was being transferred to the next level of service which I didn't have time to do as I am work.

This cannot be an isolated customer issue...there has to be a global fix to this....a setting or configuration that is not working. Since I can get text messages from my iMac to my phone...there is definitely a connection....it just doesn't recognize when I delete a message.

Hopefully someone has better luck and posts a solution.

Ditto ditto ditto. I had to give up after over an hour and then their asking me to be called the following day to have this issue elevated to engineering. This should have been caught during iOS Beta testing!

Yes, it is well-known that signing out of iCloud can have unintended consequences!!! :-)

Well, my iMac is late 2015 and I do plan to get a new iMac as soon as the new models are released... which I expect in 2nd quarter of next year, but hope sooner.

I did this, and it did not resolve the issue.

I have this exact problem. Tried turning off iMessage on all devices, etc. No change. Looking forward to Apple swiftly issuing solution.