For some reason when I delete a song in iTunes it not longer deletes the file in finder automatically as it used to.
So I have to right click on the song and choose "Show in Finder" in order to manually delete the file myself. And its a hassle.
I want my Mac to do that automatically once again.
iOS 9.3.2, iTunes
First of all thanks for replying my post.
I have both boxes checked ("Keep iTunes Media folder organized" and "Copy files to iTunes Media folder when adding to library") and still when I want to deleted a song (not from a playlist) it does not deleted the original file inside the iTunes Media folder.
How can I revert that?
I have this issue as well. Worked fine and as you described until a month or so ago. It always used to ask if I wanted to keep the file or not when deleting from the library. Now it simply deletes from the library and doesn't ask if I want to delete the file as well.
I don't have iTunes keeping my media folder organised and never have but I still used to get asked if I wanted to delete the file as well.
Or alternatively, if you are deleting from your library and the underlying file is not being deleted, that usually means that iTunes is not set to be managing your files. By default iTunes does manage your files, but you have the option to do otherwise (maybe you inadvertently changed your settings?)
Check your iTunes Preferences/ Advanced and look for the options "Keep iTunes Media folder organized" and "Copy files to iTunes Media folder when adding to library". If these are both unchecked, then (I believe) that iTunes will not delete the native file, especially if it is outside the designated iTunes Media folder.
If you find that these options were not checked, and you have media files outside the designated iTunes Media folder location, you can consolidate your library to bring all files within the iTunes Media structure:
iTunes 12 for Mac: Change where your iTunes files are stored
OK I think I have stumbled on the answer. I found a music file in the library which offers me to delete the file when I asked to delete it from the library. The difference with this file was that it's location according to iTunes was via a drive I had mapped to my NAS (i.e. B:\Ozzys Documents\My Music\iPlayer Recordings). I looked at the files which weren't offering me the option to delete and their location was not a drive letter but a straight UNC path to the NAS (i.e. \\Drobo-FS\Public\Ozzy Documents\My Music\iPlayer Recordings).em solved ... for me at least.
Problem solved .... for me at least.
If you deleting the file from a playlist, that's the correct behavior. It's removed from the playlist but remains in your library. Is that what you're doing?
When i delete a song in iTunes it does not automatically delete the file in iOS El Capitan 10.11.05
