Q: How can I delete duplicates all at once

Duplicates in iTunes are usually the result of reimporting content located outside of the media folder when your settings allow for imported songs to be copied into the media folder. iTunes doesn't keep a record of the external paths, so if you add the same folder twice you get two copies.

Apple's official advice on duplicates is here : Find and remove duplicate items in your iTunes library. It is a manual process and the article fails to explain some of the potential pitfalls such as lost ratings and playlist membership, or that sometimes the same file can be represented by multiple entries in the library and that deleting one and recycling the file will break any others.

Use Shift > View > Show Exact Duplicate Items to display duplicates as this is normally a more useful selection. You need to manually select all but one of each group to remove. Sorting the list by Date Added may make it easier to select the appropriate tracks, however this works best when performed immediately after the dupes have been created.  If you have multiple entries in iTunes connected to the same file on the hard drive then don't send to the recycle bin.

Use my DeDuper script if you're not sure, don't want to do it by hand, or want to preserve ratings, play counts and playlist membership. See this thread for background, this post for detailed instructions, and please take note of the warning to backup your library before deduping.

(If you don't see the menu bar press ALT to show it temporarily or CTRL+B to keep it displayed.)

The most recent version of the script can tidy dead links as long as there is at least one live duplicate to merge stats and playlist membership to, and should cope sensibly when the same file has been added via multiple paths.

tt2

Hello! I got really excited about this bc I'm having the same crazy issue. But when I run the Script, it tells me that it didn't find and duplicates but they are clearly there and itunes identifies them as well. Any advice? Thanks!

If you use Shift > View > Show Exact Duplicate Items in the music section of your library how many items do you see? Are you currently signed into the Apple Store? Do any of the duplicates show with cloud symbols?

tt2