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sekoitus

macrumors member
Original poster
Jun 30, 2009
56
15
Basically dying here, spent HOURS on troubleshooting this, but there's simply nothing wrong with my setup from as far as I can see.

Devices: iPhone 14 Pro (iOS 16.0.2), MacBook Pro (macOS 12.6)

iCloud enabled on both devices, logged into same Apple ID.

iPhone Settings for iCloud has everything enabled, including Keychain and Messages.

MacBook iCloud settings has also almost everything enabled, including Keychain, and in the MacBook's Messages app under Preferences / iMessages the "Enable Messages in iCloud" is enabled, and I'm properly logged into iCloud as well there.
  • If I send a message on iPhone to someone, it pops up in Mac's Messages app OK.
  • If I send a message on Mac to someone, it pops up in iPhone's Messages app OK.

  • If I delete a message on iPhone, it also gets deleted from Mac's Messages app OK.
HOWEVER...
  • If I delete a message on the Mac, it does NOT get deleted from iPhone's Messages app and I have to delete manually from the iPhone if I want it deleted there.

This is now driving me bonkers. I've tried disabling and enabling Messages in iCloud, both on the iPhone and Mac, I've tried logging out of iCloud and logging back in on both devices, but nothing fixes this. Same behavior remains.

I've googled this to no end, and seen some other people have similar problems in the past, but any of the solutions I've found hasn't helped in my case. Some people reported things like logging out of iCloud and back in fixing this, but alas, not for me.

If someone knows a suggestion what I could still try, and if it it ends up fixing this, I will goddamn buy you a pizza!
 
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addonexus

macrumors member
Jun 23, 2018
30
3
Nothing you can do and not the first time it’s happening.

I remember encountering the same problem maybe 2 or 3 years ago. Tried signing out and in Apple ID from my iPhone and Macbook; turn on and off iMessages but nothing works. Suddenly, one day it was working properly again.

So don’t waste time troubleshooting. Just wait for Apple to fix this.
 

Mac7

macrumors 6502a
Jun 14, 2009
840
104
Mine is the opposite. I delete on my iPhone but it stays on my mac.
 

scoresman903

macrumors member
Sep 22, 2022
30
7
I've experienced this intermittently as well. And I've done troubleshooting along the lines of what you have done. The issue just seems to return in a day or two after I go through the steps of logging out and back in / disabling, then enabling messages in iCloud.

Not to complicate matters, but I also have an Apple Watch and notice that SMS messages never seem to delete when they're deleted from my iPhone or MacBook Air; instead, I have to remove them manually. This is infuriating because they're all supposed to be syncing with iCloud and you would expect for the iCloud synchronization to take care of removing messages on all devices, whether iMessage or SMS.
 

sekoitus

macrumors member
Original poster
Jun 30, 2009
56
15
I love all you friendly & helpful peeps! Thank you!

Not to complicate matters, but I also have an Apple Watch and notice that SMS messages never seem to delete when they're deleted from my iPhone or MacBook Air; instead, I have to remove them manually. This is infuriating because they're all supposed to be syncing with iCloud and you would expect for the iCloud synchronization to take care of removing messages on all devices, whether iMessage or SMS.
I think this is expected? When I delete a message (SMS or iMessage) from my iPhone, it does not delete it from my Apple Watch. When I delete such message from Apple Watch, it does not delete it from my iPhone.

But they do sync otherwise with Apple Watch, i.e. new messages pop up on the Apple Watch. Just have to manually delete the messages on Apple Watch even if already deleted from iPhone.

I think I read somewhere that this is expected behavior for Apple Watch?

Can someone please confirm here if that's the case? Or does someone's Apple Watch sync also the deletions?

Seems like it's an issue with Mavericks and iOS 16 not playing well together - try downloading the Ventura beta build to see if that helps!
Thanks! i won't install the beta but will install Ventura once it is properly available through normal update. Hopefully that fixes things...
 

scoresman903

macrumors member
Sep 22, 2022
30
7
I don't agree with your thinking that it's an expected behavior. I The whole point of iCloud synchronization is for things to synchronize across the various Apple products: iPhone, Apple Watch, and MacBooks.
 
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zackattack784

macrumors member
Sep 17, 2014
64
20
This is driving me bonkers as well. I have an iPhone and 2 iPads. iCloud messages enabled on all 3. Delete from the iPhone and it deletes everywhere as expected. Delete from either iPad and it will delete on the other iPad but not the iPhone. I’ve tried everything. iCloud messages off then on. Sign out of iCloud on all 3. I even went so far as to delete all my messages to start with a clean slate and nope same behavior.

It’s infuriating how much time I’ve wasted on this.
 
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Kylo83

macrumors 601
Apr 2, 2020
4,098
13,383
It’s not working for me I’m hoping tomorrows updates will fix it
 

Fred Zed

macrumors 603
Aug 15, 2019
5,059
5,956
Florida Unfortunately
My setup is similar to yours. But issues I’ve faced is that two iMessages were not received on my iPhone but they were on my MacBook. I never even replied or messaged them via the MacBook. My iPhone is also set to forward messages to my MacBook. Weird that the MacBook received the imessages but not the iPhone huh.
 

sekoitus

macrumors member
Original poster
Jun 30, 2009
56
15
I upgraded to Ventura now and this issue is fixed. Deleting an iMessage from Mac deletes it from iPhone too.
 
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