Unable to bulk delete iMessage photos

Question

iPhone 11 iOS 15.0.1

Messages is taking up a lot of space in my iCloud storage and I would like to delete a lot of unnecessary photos in my conversations to free up iCloud storage space.

This is what I'm doing:

1. Open Messages.
2. Open a conversation.
3. Click the contact header.
4. Under Photos click See All.
5. Tap and hold any photo -> Delete -> Delete Attachment. The screen flickers and scrolls back to the top but the photo is still there. It didn't delete. If I select multiple photos and try to delete them, it works a bit but only like 10% of the photos I selected got deleted. What's going on? It takes me forever to select and delete hundreds of photos only to find out it didn't delete everything I had selected.

How am I supposed to delete my iMessage attachments en masse in order to free up iCloud stoage space? Am I doing something wrong?

I'm thinking maybe I have to disable messages in iCloud to force delete everything from iCloud but then I'm worried I might lose everything. I would do this if disabling messages in iCloud would make my phone download all messages and attachments from iCloud to my phone first, but I'm not sure if that's what will happen.

Another quirk: Open Settings > General > iPhone Storage > Messages > Other is using 500MB but if I open it I get a blank screen. What's that 500MB supposed to be? Videos and GIFs and Stickers is using a non-zero amount of storage but they're empty too when I open it.

I have 3 devices all linked to the same iCloud account: iPhone, iPad and Macbook. I'm not sure if that's an issue. I assumed if I delete an attachment from one device then it should delete from the others too.

On my Macbook I can try to bulk delete photos in a similar way, but it's more tedious and still doesn't really delete anything. Ditto my iPad.

Answer 1

I don’t think you’re doing anything wrong and think there is a/several bug(s) in code and possibly errors in your cloud-synced database that stores these message and attachment data.

If so, the repair of this damage / data inconsistency likely requires assistance Apple Engineers or support. Even if there was a bulk or automated deletion, clearing more than one media or file attachment selection at a time if you want to retain any of the conversation text is problematic at best.

In the past I followed this procedure and ended up with a worse situation, the photos “deleted” from the conversation, but still took up cloud or device space. Yours is also frustrating in that you can’t free local space or visually clean up the message the conversations.

If you don’t want to engage with support, you might be able to solve this by disabling (or enabling cloud sync of messages in settings and check other devices that participate in iCloud sync for messages against your AppleID.

In the absence of apple coding in repair and healing of this so t “it just works”, it would be nice to have a “repair” option we could engage to fix this. My experience hasn’t been solid on this front and it feels buggy to me and fragile / prone to breakage.