Album Artwork Won't Save

Hi Derek Lawrence.

As an isolation step, you may want to try creating a new iTunes library for testing purposes and add some of the same music to that including the artwork to see if it display any differently.

Open a different iTunes Library file or create a new one - Apple Support

Cheers.

Hi Derek Lawrence.

This is going to be a multi-step process.

First, you'll want to make sure those permissions are reset to their defaults so that you can move forward on a firm foundation. So, as a first step, backup and reinstall Mojave as we discussed earlier. Once you've done that, test for the issue again. As we've isolated this to something in the user data, it's unlikely that a simple reinstall will resolve the issue, but it's worth testing just to make sure.

Once you've reinstalled Mojave (and via that, iTunes) and tested again, you'll want to take these steps.

1) Open a Finder window.

2) While pressing and holding the Option key, go to the Go menu at the top of the screen and choose Library. This will open the User Library. Note that you have to have the Option key pressed in order for Library to be visible.

3) Use the search option in the upper right corner of the window and search for "iTunes." (Note that the system will likely default to This Mac instead of Library when you do the search. To the left of the search window, you'll see Search: This Mac Library. If This Mac is highlighted, change that to Library.)

You'll get a list of all of the files and folders that have iTunes in their name or content from your library. The files and folders that are user data related to iTunes will all start with com.apple.

From there it's a case of further isolation to find the offending file. When you click on one of those, you should see a file path at the bottom of the Finder window. Use that to go to the file or folder. One at a time, move them to the desktop, reboot the Mac, launch iTunes and test. If the issue is still present, move the file or folder back to its original location and move on to the next one.

It's a time consuming and somewhat laborious process, but it's the best way to hunt down where the user data is corrupt so you can resolve this issue.

Cheers.

Hello Derek Lawrence and welcome to Apple Support Communities.

I see you're having some issues with getting album artwork to save when ripping CDs to your iTunes library. You'll find an extensive discussion about how and where artwork is saved, including a response marked as Apple Recommended about how formats can influence that here:

iTunes won't let me save album artwork - Apple Community

Also, is there an active Apple Music subscription as part of the equation here? Or is everything in your library iTunes purchases and/or ripped CDs?

Cheers.

Hi Derek Lawrence.

OK, that helps. The behavior is isolated to the Mac Mini. The next step would be to isolate it further to an issue with iTunes on that device or to something in the user data. To do that, you'll want to create a test user account and then try the same thing when logged in to that account.

How to test an issue in another user account on your Mac - Apple Support

If the issue is resolved in the test user account it will be a case of tracking down what exactly in the root user account is amiss. If the issue is not resolved in a test user account, you'll know that the issue is with the installation of iTunes on the Mac Mini. If it comes to that, as iTunes is not able to be installed outside of the installation of Mojave, you'll need to reinstall Mojave.

How to reinstall macOS from macOS Recovery - Apple Support

Note that while a good backup is always a best practice before taking a step like this, reinstalling without erasing the drive is an "in place" process. In other words, you can reinstall the OS without losing the user data. (But, again, a good Time Machine backup is your best friend in a situation like this.)

Time Machine - Apple Support

Cheers.

See Repair security permissions for iTunes for Mac - Apple Community. Are you using AirPlay to listen to music at the time you're trying to make edits?

tt2

Hi Derek Lawrence.

To make sure I'm clear, are you saying that the artwork is appearing as expected on the laptop but not on the Mini? You mentioned macOS and iTunes versions but did not specify which versions those were. That info may prove helpful as well.

Cheers.

Hi Derek Lawrence.

You have mentioned a couple of times having set permissions on iTunes files. Was this issue present before you changed the permissions? In other words, was changing the permissions something you did in an attempt to fix this?

Cheers.