iTunes Cache - How Delete?

See Duplicate songs in iTunes - Apple Community for some general background. I have a Windows script that can clean up a variety of different types of duplicate. In your case you might have what I call logical duplicates where two or more entries in the library are connected to the same physical file. Organizing duplicates by date and removing the recent copies, without deleting the underlying files, may be an approach that works, but may not be so easy to apply if the duplicates have been generated over time. Backup first.

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The list of tracks in iTunes is maintained independently of whatever might be in the media folder. Deleting files from the media folder won't clean up unwanted entries in the library. In addition iTunes will typically show any unhidden and undownloaded purchases in the cloud, sometimes as duplicates to tracks that are downloaded. Signing out of the iTunes Store and then signing in again can clear these.

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Can you share a screenshot of what you see and think is wrong? iTunes should generally be managed via iTunes, not Finder. If you delete files in Finder without removing the entries in iTunes they will remain, and look like any other track until you try to play them. At that point they gain an exclamation mark to indicate a broken link and you may be prompted to try to locate them. You can select and delete the unwanted entries in iTunes.

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