Delete on iTunes not working with External Drive

[sevenseconds]

I have my iTunes Media folder on an external drive, formatted in APFS.

When I delete a song I have ripped from a CD, the only prompt I get is whether I want to delete from iCloud Music Library and nothing else. Nothing goes in my Trash. The song effectively disappears or enters some kind of purgatory.

I want to be able to view the trash on that external hard drive and then empty that trash. I am able to play tracks and movies from the external drive no problem.

Sadly, this has been going on a few months and I am only now working up the nerve to tackle it. Any help would be greatly appreciated.

 

[NoBoMac]

Might be permissions on the external drive: it can't create/access the Trash folder that is on the external drive (Trash icon is a mash-up of local and external trashes).

So, "Get Info" for the drive and make sure "ignore ownership" is checked.

If not that, might possibly how iTunes is working (doubt it though). You see this in the *nix world where external drive deletes delete immediately vs move to some sort of trash construct.