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I am on macOS Mojave running iTunes with its library stored on an external drive. Both my main machine and external drive are formatted in APFS. When I delete a song on iTunes, the file never gets moved to Trash. I now have ~1000 .mp3/.m4a files that were "deleted" but are nowhere to be seen. Some of them I want to recover from Trash and so I would like to see my Trash on the external drive.

Issues worth noting:

  • Permissions discrepancies

root of External drive

The external drive Media does not have "Staff" permissions but instead something called "System" permissions. A few months ago, I accidentally wiped this drive and had to bring it in to a data recovery place. All other drives connected to my system have a "Staff" permissions where this drive has "System."
Inside this drive is the iTunes folder which has normal permissions. subfolder inside Media drive

  • Deleting files in iTunes no longer prompts the "Do you want to delete this file from your computer as well as iCloud Music Library" prompt

Here is my iTunes preferences if this is any help. enter image description here

Does anyone have any idea how I can see my Trash again? I fear by copying everything over to a new drive that I would lose the Trash, although I'm wondering if that's the only solution and my drive is corrupted.

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