iMessage won't delete on iPhone

Open messages preferences in Mac > click on general > click on drop down arrows keep messages > select 30 days a pop up appears click on delete see the article Change General preferences in Messages on Mac - Apple Support

Hi there, danirieber.

You mentioned that you factory reset both devices. To confirm, that means that you erased your data, reinstalled the software, and then set your iPhone and MacBook Air up without a backup being restored, correct?

If that is correct, after all the steps you've taken, you can contact Apple Support for further assistance here: Contact Apple Support

Take care.

Typically erasing a device is the last ditch effort to resolve an issue. But when taking that step you want to test a new setup with no restored data. This will allow you to determine if the issue is related to your previous backup, and could potentially help narrow down the issue to a software bug or hardware issue.

Also do keep in mind that iMessage activation can take up to 24 - 48 hours on a device. This can take longer if anything changes on the carrier's end, such as changing your phone number, your carrier, or your device. I have heard Verizon say it can take up to a week for their systems to be caught up after certain changes.

If you haven't already I recommend the following: If you can’t turn on or sign in to iMessage or FaceTime - Apple Support. Apple support does have a few things they can check on the back end to ensure your account is functioning normally. So call apple support if these steps fail to address the issue.

Also, be aware many changes in iCloud are immediately available on all your devices, but some simply take time.

Having exactly the same issue...started with IOS16. I can delete messages from either the Mac or the iPad and both devices sync the delete perfectly. The iPhone 14 Pro retains the message without deletion. If I delete a message from the iPhone, the message is deleted from both the Mac and the iPad.

I have been in touch with Apple support and we have gone through all sorts of tests. It is now in the hands of the software engineers so I am told. Hopefully a fix is coming.

Same problem, iMac 24 macOS 12.6 and iPhone 12 iOS 16.0.3.

No problems before update to iOS 16.0.x (clean install without Backup).

Spent several hours but no solution found.

Hope Apple will fix this immediately!

I am also having this problem. Running latest version of OS on my Mac, iPad, and iPhone. When deleting message or conversation on iPhone, it instantly deletes on all my devices. If I delete on my Mac, it does not delete on my iPhone. At this point I'm subject to do all my deletions on my iPhone just to keep everything in sync.

I have learned to just delete from the iPhone always...helps my sanity! Ha!