iTunes 12.9 loses album artwork after every update

This is a separate issue from the artwork problem. Ideally we'd be discussing this in a separate thread. As long you have a backup it will be possible to recover. I suspect the easiest steps will be these.

1. Close iTunes, hold down option while launching iTunes and use the option to choose or create a new library. Click create.
2. Enable iCloud Music Library if in preferences if it isn't already on, let iTunes populate with your cloud library.
3. Delete all content from your iCloud library that has the wrong value for Album.
4. Use File > Library > Update iCloud Music Library to ensure the changes are synced to the cloud.
5. Disconnect from the Internet and close iTunes.
6. Restore your backup, launch iTunes with option held down and connect to the restored library.
7. Disable iCloud Music Library in preferences.
8. Reconnect to the Internet, enable iCloud Music library.

This assumes that all of the affected content you need to repair was stored locally on your computer and will be available after you restore your backup. If you were keeping your content in the cloud we will have to look more closely at a scripting solution.

To be continued in Album Artwork Unremovable - Apple Community.

tt2

You're certainly not alone, but neither is it a common issue. iTunes was doing something funky with non-square images a build or two ago but I didn't really get to investigate that one as all of my images are square. You could try Re-Embed Artwork from Doug's AppleScripts for iTunes which might refresh the thumbnails as a side effect of its activity.

tt2

First off, after deleting the Album Artwork folder, did you also empty the trash? If not iTunes might still be using the old cache folders.

If this library has been migrated from a previous computer another possible issue could be security permissions.

Make sure that your profile has full read and write permissions to the iTunes folder and all subfolders. Use Get Info on the iTunesfolder in Finder. Click the lock at the bottom right to make changes. Make sure that Locked isn't ticked and that your own account has Read & Write access, then use the gear icon to Apply to enclosed items and confirm.

tt2

Did you apply to enclosed items anyway? This forces the permissions to be updated on each subfolder. There is no way to tell by looking at the top folder if they are already set correctly everywhere inside. You can try scrolling through the library in different views to see if it will reveal what is embedded. You can also select the library and use the right-click > Download Artwork option to have it try to download art for anything that doesn't have it embedded already.

tt2

I realize this will sound crazy BUT I was having this problem today, and the only thing I could figure out was that I had recently connected to my new AppleTV over Airplay. I disconnected and was able to update and save new artwork!

Amighty, you mad genius. You have saved me much $$ in therapy. This just started happening today. I disconnected from Airplay and suddenly I can save changes again. Must be heavy sunspot activity or something...?

I'm having issues with this still. I was connected to a bluetooth speaker and turned off the airplay and this did not fix the issue. I'm especially irritated with this issue because it currently is using an old vehicle renewal receipt as the album cover (I have no idea how that happened). When I go into the "get info" menu I've tried deleting the artwork several ways:

selecting the artwork and hitting the "delete" [backspace] key

selecting the artwork and using keys, "command" + "X"

selecting the artwork in the top left corner and hitting the "delete" key

nothing's worked currently.

I've tried restarting iTunes,

dragging the album artwork I want over the previous image.

I've gone under the first song in the album, clicked get info, went under artwork and added the artwork to each song individually, then clicked "ok."

Again, nothing working.

Any help you can think of?

I'm using a Mac 10.14.3 & iTunes 12.9.2.5

This is an issue with just 1 album; however, last night in my attempt to fix it I've now somehow managed to rename half of my library to that album. This happened when I tried to merge two albums (one of which is the album in question and another with the same title) by highlighting the two of them, selecting "get info", under details in the "album" line I typed the album title I wanted them both under so they would merge. When I clicked "ok" it processed and then half of my library has that album title.

This change has updated my library in the cloud also.

I decided the quickest way would be to restore my library from a backup I have. I deleted the library and reinstalled it but when it started to sync with the cloud the cloud started overwriting the actual album titles with the messed up one.

Is it only the Album titles that have been messed up? I have an existing Windows solution that I might be able to adapt for Mac. You would restore a backup while offline, export the data that has been corrupted, then reconnect to the active library and import the saved data, assuming I can make it work. Another approach would be to remove all of the damaged content from the iCloud version of your library (might be easier done in a new empty library connected to the cloud), then sign out of iCloud Music Library, restore your backup, then sign in again. At this point the libraries should be merged so if the cloud library has no bad data it cannot overwrite the library you restored.

tt2

Honestly, I think this is not quite the same issue that the post started with - it sounds like you have some bad files. If you can get your library back to where it was before (there should be backup library files somewhere, but if you have "keep my iTunes library files organized" clicked you might be SOL) the easiest thing to do would be to delete and re-digitize them or re-download them or something similar. Also, I have had some strange issues with certain tracks and albums before because iTunes had somehow put information into the "work" field of the song data. Sometimes the genre ends up in there, or sometimes the album title does, and it looks fine in some places and is totally bonkers on the iPhone. If you"get info" on those tracks you can check the "show work and movement" button and if there's any info in there, clear it out and you will be all set.

No, some albums have been merged also. I.e. A movie soundtrack album has another video game soundtrack listed as part of that album.

How do I export the corrupted data?

finally, I got off the phone with apple support and someone is going to call me back. Unfortunately, however my iCloud version of my library has also been affected. I deleted and replaced the iTunes folder with my backup and once it synced with my library it changed the albums into their corrupt state.