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After enabling iTunes Match, songs that are recognized as duplicates are marked with an icon:

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Clicking on this icon brings up a dialog offering to delete the duplicate:

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Does "Delete Duplicate" do anything different from simply deleting the file in the usual way? In particular, since this approach does not support deletion of multiple files, can one simply select all files marked as duplicates and delete them to achive the same effect as clicking on these icons one by one?

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Careful. There seem to be issues as to what iTunes selects as a Duplicate. If you delete any files - make sure that you search the song first. You may be being asked to delete a higher quality version or your DRM-free version.

Don't delete any until they issue an update or more reviewers have spoken!!!

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Yes, that often happens, but if you delete both, and redownload, you'll end up with the high bitrate DRM-free version. – raxacoricofallapatorius Nov 17 '11 at 16:10

The ways in which iTunes and iTunes Match identify duplicates is frustrating and outdated. If you have a track appear in two separate albums, iTunes Match will indeed identify it as duplicate tracks. I have been forced to use third party software to get rid of iTunes duplicates for real and recover tracks which were deleted by iTunes but were not duplicates.

You might want to have a look at this iLounge article concerning iTunes match. Look especially where it refers to the way in which iTunes Match identifies duplicates.

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