transferring music from mac os x 10.6.8 to mac high sierra 10.13.6

I'm going nuts, guys. I've tried transferring music from iTunes on my old mac (os x 10.6.8) to my new one (high sierra 10.13.6) and nothing but weird things have happened. Not only do I still not have the old music on my new computer (after trying with migration assistant and apple music) but now I get an incessant message saying "The iTunes Library file cannot be saved A duplicate file name was specified" that pops up repeatedly no matter what I do, even though iTunes seems to work fine. I've also notices that files I keep deleting from my library show up again every time I open iTunes.


I'm ready to restore iTunes to factory settings, no loss for me there. But does anyone have any tips for how to move my music over from my old laptop? Please and thank you!

MacBook, 10.13

Posted on Feb 16, 2019 10:12 AM

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Question marked as Top-ranking reply

Posted on Feb 17, 2019 1:57 PM

Hello rachlita,


Thank you for using Apple Support Communities! I understand that you're experiencing issues transferring your iTunes library to a new Mac. I would be happy to help point you towards a resolution.


If the music in the iTunes library on your older Mac was imported from sources such as CDs, and not from Apple Music or the iTunes Store, we'll want to start by having you consolidate and back up your library:


Back up and restore your iTunes Library - Apple Support


After that, follow the steps in the resource below to move the iTunes library to the new Mac:


Move your iTunes library to another computer - Apple Support


Music that was purchased from the iTunes Store can be redownloaded to the new Mac following the steps under the "Redownload movies, TV shows, or music" section here:


Redownload apps, music, movies, TV shows, and books from the App Store, iTunes Store, and Apple Books - Apple Support


If you use iCloud Music Library with an Apple Music subscription, this allows you to sync the Apple Music version of a song to a new device, however it will not transfer the original media. This means that if you were to cancel your Apple Music subscription, the songs would no longer be available on the new Mac. Let us know what happens from here.


Take care!


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Question marked as Top-ranking reply

Feb 17, 2019 1:57 PM in response to rachlita

Hello rachlita,


Thank you for using Apple Support Communities! I understand that you're experiencing issues transferring your iTunes library to a new Mac. I would be happy to help point you towards a resolution.


If the music in the iTunes library on your older Mac was imported from sources such as CDs, and not from Apple Music or the iTunes Store, we'll want to start by having you consolidate and back up your library:


Back up and restore your iTunes Library - Apple Support


After that, follow the steps in the resource below to move the iTunes library to the new Mac:


Move your iTunes library to another computer - Apple Support


Music that was purchased from the iTunes Store can be redownloaded to the new Mac following the steps under the "Redownload movies, TV shows, or music" section here:


Redownload apps, music, movies, TV shows, and books from the App Store, iTunes Store, and Apple Books - Apple Support


If you use iCloud Music Library with an Apple Music subscription, this allows you to sync the Apple Music version of a song to a new device, however it will not transfer the original media. This means that if you were to cancel your Apple Music subscription, the songs would no longer be available on the new Mac. Let us know what happens from here.


Take care!


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transferring music from mac os x 10.6.8 to mac high sierra 10.13.6

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