iMessages reappearing after Deletion/Not syncing across MacBooks

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Level 1

19 points

iMessages reappearing after Deletion/Not syncing across MacBooks

Hello All,

18.5 iPhone 16 Pro Max/2025 MacBook Air/2023 MacBook Pro

iMessages/Messages not syncing properly when I travel is the issue across devices.

For example, Pro laptop remains at office, hardwired ethernet/power and set not to go to sleep. I also leave the Messages app open and do not select a message. I travel with my iPhone and Air which for the majority of the time do sync up correctly. Every now and then deleted messages that have not synced up with the Pro will randomly show up again on my Air or my iPhone. These are messages that I've deleted from my iphone or my Air while traveling and will reappear on the Pro after I return from traveling. I have to re-delete them in order to manually have all 3 devices sync back up.

I have the iPhone messages setting "Keep Messages" set to 30 days, Messages in iCloud turn On, on both laptops.

Seems that when I delete and also remove from Recently deleted from Message they are not deleted and are stored somewhere... and repopulating even past the 30 days setting.

If anyone is experiencing something like this please chime in. Just got off the phone with senior tech who suggeted it could be a bug and they are working on it but he wasn't sure...

iPhone 16 Pro Max, iOS 18

Posted on May 13, 2025 4:03 PM

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Answer 1

SoCal_Edwin Author

Level 1

19 points

May 21, 2025 5:29 PM in response to Toyota-devotee

I have the iMessages setting to 30 days.

What was recommended from Apple Tech Support was to leave the iMessage setting to keep for 30 days, wait for 30 days to pass (this, according to them will wipe out ALL stored/archived Messages (iMessages & Text Messages)

After the 30 days re enable the setting to 30 days again and I should not see any archived messages because the "system" will only keep the messages for 30 days then purge them.

And all devices logged in with my ID (iMessages enabled) will sync accordingly.

It was a little confusing, but I'm on the fence if it will work.

I'm willing to look into any options, but I think it's a bug that Apple users have not stumbled across yet...

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Answer 2

May 21, 2025 7:57 PM in response to SoCal_Edwin

Theoretically, it makes sense with a little clarification needed on the part where you say after the 30 days are up that you should “re-enable” 30 day because I don’t think you turned some other setting off at any point and so I’m not trying to be nippy again just trying to clarify to make sure you didn’t forget to at some point change that to something other than 30 days. My guess is that you just leave it in that setting and then after the 30 days has passed anything older than that would have automatically been deleted. So I guess you’ll know in 30 days if something remains or not. I know that when I delete a bunch of messages and then I look into the “recently deleted” and click on “clear all” then that will seem to permanently remove them, but then it makes room for a bunch of others that I have never taken the extra step to “clear all” to repopulate, but that’s what I want in my situation because this is an elderly person who forgets everything so it’s good to be able to reference back to what people have said and that is why for this particular person when I set up their phone for them in the settings on iMessagesI have selected “keep forever”

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Answer 3

SoCal_Edwin Author

Level 1

19 points

May 21, 2025 8:19 PM in response to Toyota-devotee

No problem on being nippy picky, being detailed is a good thing in trying to figure out this issue.

My bottom line is that for me iMessages do not sync across my 3 mostly used devices, iPhone, Mac Pro and Mac Air. I travel with my phone and Air and the Pro remains at the office. When I delete messages and clear them from the recently deleted tab (when traveling in the US) And I return back home, random deleted messages will reappear even those that are past 30 days.

I am the type of person once a conversation or task is completed that has been initiated via text, I delete the conversation as to not get bogged down with multiple strings of endless messages (that also take up space on the phones storage) Its a way for me to keep organized.

I am not an elderly person who forgets everything, I'm a person who tries to stay organized and up to date with my tasks and conversations. I am not the only person as I have tried this with my wife's account and I have gotten similar results.

I have also tested with with friends accounts who like you say, have the "forever" option enabled and I have been able to reproduce some missed sync issues but no where near the same as I have with mine when I travel.

I am curious to see what happens after I have disabled Messages in iCloud and I have past the keep messages for 30 days will the phone when I re enable message in iCloud and the 30 days will past messages from beyond the 30s still populate or show backup on the phone. If thats the case, my guess would be correct that Apple is storing messages that have been delete for past the 30 setting I have set the phone to do.

Wouldn't be the first time a tech company says something and does something else...

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Answer 4

May 21, 2025 5:03 PM in response to SoCal_Edwin

I believe this is because you have your settings on your iMessage as keeping them forever as opposed to the one year option or 30 day option

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iMessages reappearing after Deletion/Not syncing across MacBooks

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