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I have collected about 50GB of music on my PC across a few folders with plenty of duplicates.

I just installed iTunes and synced an iPhone and its associated iTunes/Apple ID account, which created a library and copied a few hundred songs into it.

Is there a way to import all music from designated folders on the PC into iTunes, including de-duping?

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To import music copy it to the folder \iTunes Media\Automatically Add to iTunes

Apparently there is no native bulk deduplication functionality.

One can identify duplicates within iTunes by going to View -> Show Duplicates.

However to bulk deduplicate presently one needs to find third-party utilities. Most are not free.

I tried the shareware iTunes Duplicate Song Manager, but not only did it miss about half of the dupes found by commercial programs, but it also failed to remove them from the iTunes index when it removed the files. For $12.95 Dupe Away managed to clean everything up and find the other obvious duplicates.

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    TIL about "Show Duplicates" - thanks! Small correction: the page you've linked to now says that "Show Duplicates" has moved to File > Library > Show Duplicate Items, which I can confirm is the case in iTunes 12. – Kendall Lister Jun 9 '19 at 1:14

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