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)