iTunes 12.5.1.21 Move to Trash Not Working

I usually hold Option when I delete tracks from a playlist in iTunes in order to permanently delete a file in my library. When I do this, iTunes always asks if I want to keep the file or move it to the trash. I always select Move To Trash just in case I accidentally deleted something important, or I've changed my mind about the file and want to be able to recover it from the trash.


The behavior I'm currently seeing with iTunes 12.5.1 is that when I choose Move To Trash, the file(s) never go to the trash, they're just permanently erased from my computer with no trace in sight. Files go into the trash from Finder without issue when I use Command + Delete. I'm not sure why iTunes is destroying the file after I choose Move To Trash. This started happening after I updated to MacOS Sierra. It was fine on El Capitan. Has anyone else experience this? Is there a way to fix it?

Mac mini (Late 2012), macOS Sierra (10.12)

Posted on Sep 29, 2016 4:39 PM

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4 replies

Mar 15, 2017 7:46 AM in response to bootcockie

Same problem here. New MacBook Pro OS Sierra 10.12.3 iTunes 12.5.5.5. I even hit "Empty Trash" and saw no files change on available GB path bar. The total gigs of the drive stayed the same after I emptied trash. I then restarted computer and now see all the tracks in the trash. So the original "Empty Trash" did nothing. The files were in a state of digital purgatory. But this is defiantly an error!

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iTunes 12.5.1.21 Move to Trash Not Working

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