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Hi Colette, Downloading music from itunes to your walkman is not possible. If you are using a PC, I would suggest for you to use the Music Center app or you can also transfer content directly from Windows Explorer to your Walkman by drag-and-drop. And if you are using a Mac, try to use Content Transfer app. Kindly check the link below for additional information. Thanks! https://helpguide.sony.net/dmp/nwe390/v1/en/cover/level2_03.html Regards, Sam Sony Social Support
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