iTunes Duplicates of Same File

Try iTunes > Preferences > Advanced > Reset Warnings. iTunes should be able to give you an option as to whether or not the file associated with the deleted item is also removed from the media folder.

tt2

Hi mcarduner,

Welcome to Apple Support Communities. We understand you're seeing duplicate songs in your iTunes library.

It's important to organize your iTunes library, and we'll be happy to help.

Are you seeing duplicate files for music content that was purchased in the iTunes Store? Also, are you an active subscriber to Apple Music? If so, we recommend to turn on Sync Library and see if that helps remove the duplicate songs that appear in your iTunes library: Turn on Sync Library with Apple Music

Please let us know if that helps.

Kind regards.

See Duplicate songs in iTunes - Apple Community. You need to manually select and remove all but one of each set of duplicates without deleting the underlying files. It may be relatively easy if you display exact duplicates only and sort by date added. If there is clear pattern of new tracks added on a certain date then it should be easy enough to remove them. Back up first.

tt2