Deleted files from iTunes on External Drive but not ending up in Trash

[sevenseconds]

I'm having a problem with a 4TB OWC external drive that I use as my iTunes media folder. It's APFS formatted.

When I delete a track from iTunes, I don't get asked whether I want to permanently delete the track or just remove from iTunes. I just get asked whether I want to delete from my iCloud Music Library. These are .m4a files that I had ripped from CDs years ago.

The bigger problem is, nothing goes into my Trash. So I've now deleted hundreds of tracks recently but can't see any of the tracks I've deleted.

I would like to view the trash where all these tracks are and then delete them. There may be a few I want to recover/restore.

I've tried repairing permissions on the drive and no errors were found.

I see a lot of conflicting or outdated threads on this topic which is leading me to write this post. Thanks in advance for your help.

 

[Juicy Box]

There is a setting in iTunes like "copy files into itunes library", or something similar.

Is that turned off?

 

[sevenseconds]

There is a setting in iTunes like "copy files into itunes library", or something similar.

Is that turned off?

No it’s turned on. Thanks for asking

 

[Juicy Box]

I would guess a permission issue. Or maybe your external disk is locked?

I have had a lot of issues in the past with using external drives for my iTunes Library. I don't know if it is related, but most of those issues started after the release of the iCloud Music Library.

I got tired of dealing with it, so I just started using PLEX for everything.

 

[sevenseconds]

I would guess a permission issue. Or maybe your external disk is locked?

I have had a lot of issues in the past with using external drives for my iTunes Library. I don't know if it is related, but most of those issues started after the release of the iCloud Music Library.

I got tired of dealing with it, so I just started using PLEX for everything.

I hear you. I just have a 10+ year old, 3TB library so it would be a real pain to move to another platform. Everything works good, it's just I can't see the Trash.

I tried changing permissions on the external drive but that hasn't done anything:/