Messages older than 30 days are not deleted

Changing to "keep for one year" then "keep for 30 days" worked for me assuming it was not a coincidence. I tried "keep for 30 days" 6 or 7 times, bouncing between my Mac and iPhone but then the first time I used 1 year on the Mac and then immediately switched to 30 days it worked.

Ok, I appear to have managed to get this to work, I’ve shrunk my iMessage iCloud store!

my original setting was “keep everything”.

I had 5 devices signed into iMessage, 2 of which I didn’t need, so first I logged them out (disabled iMessage and powered down the devices).

then I brought up the settings for how long to keep messages for on my Ventura iMac 27” 2017, M1 MacBook Air and iPhone 16 pro max.

I toggled keep messages from 1 year to 30 days (I’d tried 1 year already and it didn’t do anything) and back again on all three, noting that the 16 pro max and the M1 air updated each other, but the old iMac didn’t. I manually fixed that one.

I then discovered via iCloud on web (and a lot of refreshing) that the 2.4GB of message storage was shrinking.

despite flipping to 1 year and back, it has deleted everything older than 30 days, but I’m hoping at this point it’ll manage a rolling 12-month window, which is great.

so it can work, but I suspect the iMac, or the extra older devices, may have been part of the problem.

I get annoyed every time I need to do this, jumping thru hoops. Apple makes it really easy to grow storage size but really hard to trim it. Call me cynical but they are not bashful at encouraging profitable storage upgrades.

The only reason I use 50 GB is for Private Relay. If they had it at 5GB I would done mode today. I don't store anything in iCloud that if it got lost on iCloud servers I'd be SOL of ever seeing it again so I store locally. I have read to many people losing data on iCloud to trust the platform.

If that’s in fact true, it’s not a very practical solution.

What did you see on iCloud?

especially if you an send images in full resolution up to 100MB in size.

Well here is what worked for me: First I said to keep one year, then changed it to 30 days. THEN it worked to delete older than 30 days!

I tried that it still didn't work.

Are you sure this worked? I’ve just come across this issue as well. Can’t seem to get iMessages to delete messages.

Tried that it didn't work. Really wish Apple would fix this bug.