Delete photos from Messages info window on Big Sur fails

This question has been asked many times in different incarnations, but I have not found an open thread.


To reduce storage on iCloud, I need to delete photos and attachments that are stored by/for Messages.app. My Macs are running Big Sur 11.6.1, and "Messages in iCloud" is enabled (to allow automatic sync between iPhone (iOS 15.1), iMac and MBP). In Messages, I select the person/conversation and click the "i" in the upper right corner. This opens the info screen, I scroll down to the Photos section, right click on one Photo or attachment opens the menu which offers "Delete". A confirmation screen pops up, and after confirming "Delete Attachment" the selected photo should be removed (ideally for all devices that are in sync via iCloud).

However, I have quite many photos that simply stay, not matter how often I try delete.


Any suggestion what to try?


Clicking the button "Sync now" in the iMessage Preferences does not help.

MacBook Pro 15″, macOS 11.6

Posted on Nov 1, 2021 2:13 PM

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3 replies

Nov 5, 2021 8:07 AM in response to mario49

Hi mario49,

thanks for your reply!


1) I have reported the problem for a MBP running Bis Sur, not for an iPhone. The answer regarding restart (or even boot into save mode) is that this does not help. This is true for all three devices (see below).

2) There are some photos (or more general attachments) that I can (or better could) delete, but there are several photos in several threads that simply stay and resist delete.

3) Since my iMessage data are synced between three devices (MBP, iPhone-SE & iMac24 as DeskTop), I have also attempted to delete the "resisting" photos on the other devices. But they are also staying on the iPhone (iOS 15.1) and on the iMac24. In fact, depending on the threat, there are sometimes different numbers of "delete-resistant" photos shown for the identical thread. That means, at least some of these photos are not in sync via iCloud although "Messages in iCloud" is enabled.

4) I have been unable to check for each and every affected photo, but in quite some cases the photo is shown in the info screen (shown after clicking "i" in the upper right corner), but *not* in the thread itself. In some cases, there are "placeholders" for photos like squares or file-icons with a question mark visible in the thread, but not the photo itself.

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Delete photos from Messages info window on Big Sur fails

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