On occasion, for one reason or another, iTunes seems to have a link to a file that no longer exists. Your options are then to either hunt for the file manually, one by one, or manually hunt and delete all the dead ones. There is a handy exclamation point icon that will tell you which are broken, but there is no way to filter for these. Fortunately, thanks to a bit of logical jiggery pokery, you can use Smart Playlists and a cunning quirk of iTunes to do it for you. Herein lies a step-by-step guide to finding all those annoying broken links. Step 1 Create a new Smart Playlist with a single Artist Does Not Contains rule. Put some garbage into the search field so it will return every artist. Call this playlist "All Music". Step 2 Create a normal playlist called "Working Music". Step 3 Create a Smart Playlist with 2 rules. These are: Playlist - is - All Music Playlist - is not - Working Music ...