How do I set iTunes to delete a song from my computer when I delete the song from iTunes?

Barryedmund, I believe you can permanently delete songs from your iTunes, erasing them from your computer. If you want to do this, go to your iTunes library and delete the song. You will be prompted with a question, asking if you want to permanently delete them (it will only ask you if you want to permanently delete the song IF AND ONLY IF the file is located in the iTunes music folder.

If it is located elsewhere you can only remove it from your iTunes (and not your computer)...I'm guessing this is the problem you're facing. If the file is located in your iTunes music folder, you will be asked if you want to keep the file on the computer or move it to the recycling bin. My advice is to consolidate your library.

Get all of your music files in the iTunes folder and you should be able to permanently delete them without a problem. Best of luck!

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