A:Answer Hi Marilyn, you may download our Media Go or Content Transfer (MAC) software which supports iTunes. Alternatively, you may drag and drop files to this Walkman using your computer's file explorer. To answer your questions, we recommend that you use iTunes to manage your files and purchase music then transfer them to this Walkman with the use of Media Go or Content Transfer. You may refer to pages 99-111 of this link for more information: https://docs.sony.com/release//Help_4579798111.pdf Thanks, -Mark