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Whenever I purchase music on my phone and then sync with iTunes later, a duplicate "Purchased on iPhone" playlist will be created. The first one will have everything I've purchased in the past, and the duplicate playlist will have the one or two songs that I just purchased.

In the sync options I checked/unchecked the box to have the playlist sync and not sync with my phone. No matter which option I choose I'll always have duplicate playlists when I sync with iTunes.

How can I fix this? I don't want a duplicate playlist to be created every time I sync. If I purchase a song on my phone I want it to be added to the existing "Purchased on iPhone playlist".

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I'd try reinstalling iTunes. Unless you're backed up and restored your iPhone between syncs it sounds like a bug in iTunes. You can remove and reinstall iTunes without affecting your library.

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