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iPod Tip: Find and Delete Duplicate Tracks
After you've used iTunes for awhile, you're bound to end up with at least a few duplicate tracks—songs you've inadvertently burned or downloaded more than once. This isn't a big deal when you have a large hard disk, but it is a problem when you're working with the limited storage space on an iPod shuffle or nano.

For this reason, it pays to periodically go through your library and delete those duplicate tracks, freeing up space for newer music. You could do this manually (yuck!), or let iTunes automatically find the duplicates for you (yay!).

To identify duplicate tracks in your iTunes library, select View > Show Duplicates. iTunes will display all tracks that share the same name, in alphabetical order. Examine each of the duplicate tracks, and delete one or more instances as necessary.

Keep in mind, however, that just because a track has the same name as another track doesn't mean it's a duplicate. Sometimes you'll have the same song from different artists, or from the same artist on different albums. So don't automatically delete a track that looks like a second copy; take your time to determine whether it really is a duplicate before you hit that Delete key.