Q: Is there a way to delete songs from iTunes and my hard drive at the same time? Currently, I have to right click on the song, select ‘Show Song File’, delete the song from Windows Explorer, and delete the song from the iTunes library. Is there a more simple process to do this?
A: There is a much easier way, indeed. To delete a song file from within iTunes’ Library window, simply highlight a song (or multiple songs) and press your keyboard’s Delete or Backspace key. iTunes will then prompt you as follows:
Select “Remove”, and you’ll see the next prompt:
Here, select “Move to Trash,” and iTunes will fully delete the file from your hard drive.
It is a little known fact that this process can also be initiated when deleting songs from smart or manual playlists: simply hold down the “Option” key (Mac) or “Shift” key (PC) while pressing Delete.