Deleted Messages Attachments Repopulating

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Level 3

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Deleted Messages Attachments Repopulating

I've had the same issue with deleting items from conversations Messages from device to device (and Mac to Mac) since the dawn of iCloud syncing. There are plenty of threads reflecting bits and pieces of the same issues, but still not a good resolution.

How this works in Photos:

If you have syncing for Photos turned on, deleting a photo or video from any device in your Photos app properly deletes the photo from iCloud (moves to deleted box where it sits for a bit (30 days, as I recall) before permanently deleting). This syncs across all devices using iCloud to manage Photos, so deleted photos on one device delete on the others as well.

The Ongoing Problem In Messages:

If you have syncing for Message turned on, deleting a photo or video from a conversation on any device in your MESSAGES app FAILS to delete the photo from iCloud (does NOT move to a deleted box where it sits for a bit before permanently deleting). There is NO syncing for deleted photos or videos from a conversation across all devices/Macs. The photo(s) and/or video(s) only delete from the device/Mac you've deleted them on...and temporarily at that because if you have iCloud syncing turned on for Messages, the photos and videos repopulate in your conversation. Apple has never fixed this and, to my knowledge has not been very clear on this issue.

The instructions I've seen from Apple are very vague on this. Essentially, it's a wonky work-around. From what I'm seeing, you'd need to:

1) Turn off Messsages syncing on ALL devices and Macs that are connected to your iCloud account,

2) Delete all of the items on every single device, then

3) Wait 30 days for the items to actually purge, then turn all devices back on.

SOOOOO...you would have to lose syncing across devices for 30 days?

One more related issue: on MACOS (not iOS), after pressing "i" on a conversation to see all pics/videos, then carefully selecting a bunch of pics/photos and pressing delete only deletes ONE item (I believe the first selected in the group). This has been an issue for years and still what I see today on an M2 Pro running Ventura.

Shouldn't deleting items from Conversations just sync like deleting Photos via iCloud (described above)?

Mac mini (M2 Pro, 2023)

Posted on Sep 23, 2023 2:08 PM

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Answer 1

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tygb

Level 9

64,748 points

Sep 24, 2023 5:41 AM in response to Adam F

You can attach photos from system photo library of photo application to the conversations in messages app .

When you delete the attachment ( photos from conversation ) , it will be separated and not moved to recently deleted , as if you delete photos from Mac A , it will be simultaneously delete from Mac " B ".

And moved in recently .

You mentioned -

If you have syncing for Message turned on, deleting a photo or video from a conversation on any device in your MESSAGES app FAILS to delete the photo from iCloud (does NOT move to a deleted box where it sits for a bit before permanently deleting).

Deleting a photo from conversation will delete ( separate the photo ) from conversation , yet conversation will still be saved , and it will not affect photos saved in www.icloud.com , for deleting photos from iCloud you can delete from photo library of Mac .

Photo application and message application function differently .

It will not happen because you have set up photo library Set up and use iCloud Photos - Apple Support and its preferences Change preferences in Photos on Mac - Apple Support and designated the photo library System Photo Library overview for Photos on Mac - Apple Support .

Photos are saved on iCloud server , once you delete photos from www.icloud.com it will simultaneously deleted from Macs .

Click on photo as shown in messages ( as shown in the screen shot ) , and click on delete key on the keyboard .

You also mentioned .

One more related issue: on MACOS (not iOS), after pressing "i" on a conversation to see all pics/videos, then carefully selecting a bunch of pics/photos and pressing delete only deletes ONE item (I believe the first selected in the group). This has been an issue for years and still what I see today on an M2 Pro running Ventura.

Use command and A keys , this will select conversation + bunch of photos , you have to select each photo and delete Delete messages and conversations in Messages on Mac - Apple Support

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Answer 2

Adam F Author

Level 3

614 points

Sep 28, 2023 1:02 PM in response to tygb

I appreciate the response, @tygb, but I'm not sure it's accurate responding to what I've described. I'll elaborate below.

tygb wrote:

You can attach photos from system photo library of photo application to the conversations in messages app .

When you delete the attachment ( photos from conversation ) , it will be separated and not moved to recently deleted , as if you delete photos from Mac A , it will be simultaneously delete from Mac " B ".

And moved in recently .

It sounds like you suggested that if you attach a photo from the Photos app to a Message, then delete that photo from a Message, the conversation remains while the photo is deleted. In the OP, I explained that a photo deleted from a conversation remains attached to the conversation on all other devices. This happens whether or not the photo came from the Photos app or another source.

. . .

Deleting a photo from conversation will delete ( separate the photo ) from conversation , yet conversation will still be saved , and it will not affect photos saved in www.icloud.com , for deleting photos from iCloud you can delete from photo library of Mac .

This is a bit ambiguous. Maybe we're saying the same thing, but it sounds like you're suggesting that going into the Photos app and deleting a photo that's been attached inside of Messages will delete that photo in Messages. That would be interesting, but it's not accurate.

Photos and Messages both store photos in iCloud (if enabled). I believe they are mutually exclusive. The original post explains that deleting a photo in Photos deletes syncs across all devices while deleting a photo attached to a Message (regardless of where the photo originated), does NOT sync across devices.

OP:

One more related issue: on MACOS (not iOS), after pressing "i" on a conversation to see all pics/videos, then carefully selecting a bunch of pics/photos and pressing delete only deletes ONE item (I believe the first selected in the group). This has been an issue for years and still what I see today on an M2 Pro running Ventura.

tygb wrote:

Use command and A keys , this will select conversation + bunch of photos , you have to select each photo and deleted

CMD-A generally would selected ALL, but I don't believe that command exists within Message (probably to avoid accidentally wiping out all conversations). However, it's not applicable here. This part of the OP explains the issue referenced in this pic:

Once "Delete" is pressed, all selected videos and pics are NOT removed from the conversation. ONLY the LAST of the group (not the first, as I thought in the post) is deleted. The rest remain. (again, that one deletion does not synch any other devices). This is a bug in MacOS (which I've reported). Doing the iOS equivalent (selecting a conversation -> Pressing the person/group name at the top -> scrolling down -> selecting a group of photos/attachments) DOES delete all attachments. (The same issue with the failure to sync across other devices remains.)

...AAAANNNND....then they typically repopulate since iCloud fails to sync deleted attachments in Messages conversations in the way that Photos syncs deleted photos.

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Answer 3

tygb

Level 9

64,748 points

Sep 28, 2023 7:42 PM in response to Adam F

, I explained that a photo deleted from a conversation remains attached to the conversation on all other devices. This happens whether or not the photo came from the Photos app or another source.

The attachment ( photos will remove from primary Mac " A " but remain in Mac " B " ) , deleting conversation will delete from both Macs .

Send you feedback Bug Reporting - Apple Developer

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Answer 4

Adam F Author

Level 3

614 points

Jun 2, 2024 10:06 AM in response to tygb

Jumping back in here to log what I'm seeing at this point. Regarding attachments in Messages:

1) I Turned off iCloud storage for Messages on ALL devices.

2) Deleted lots of attachments to Messages on my iPhone.

3) Reconnected Messages on the iPhone and allowed to sync

4) Attachments were deleted from iCloud (gained storage back)

5) Turned Message syncing back on in other devices

5) Here's the FAIL: Deleted Messages attachments remained LOCAL on MacOS. 🙄 They're not in iCloud, but still sitting on my HD and part of the conversation on that device. So, the problem above remains. iCloud is not able to delete attachments when syncing is on as Photos can. At the same time, iCloud didn't pull the Local images I deleted from the iPhone back from this Mac (connected after the iPhone synced). So, there's gotta be some kind of modification check going on. iCloud just doesn't seem to be bi-directional (it's not deleting local attachments that have been removed from iCloud).

NOTE: If you go into System Settings in MacOS -> About -> Storage Settings -> Messages you can SEE (using preview) attachments and delete them, HOWEVER you cannot see the Conversation you are deleting the attachment from by name. I'm guessing this would only delete Local (unless you've turned off Messages syncing on all devices as described above, then deleted, then turned messages syncing on the Mac instead of another device).

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Deleted Messages Attachments Repopulating

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