If you bought music through the iTunes store, the files are in a protected format--MP4--that only iTunes can play. That means that if you have a generic MP3 player, you won't be able to play the protected iTunes songs on the device. If you have an MP3 player that will not play iTunes music, you need to convert it to an MP3 file via iTunes. The software to convert these music files is free, but it may take a while to fully convert all of your music files to MP3 and then transfer them back to iTunes as MP3s.
InstructionsPreferences>Advanced>Burning."
3. Go to "File>New Playlist" in iTunes to create a new playlist. Drag and drop the files you want to convert into MP3 format into this playlist.
4. Insert a blank CD-R into your computer's drive.
5. Click on the "Burn Disc" icon in iTunes to burn the music to MP3 format.
6. Open and close the CD-ROM drive, and iTunes will automatically ask you if you want to import the CD. Click "Edit>Preferences>General." Click on the "Import Settings" button. Choose "MP3 Encoder" from the drop-down menu and click "OK." This will make the CD import as MP3 files. Select "Import CD," and iTunes will import the music as MP3s.
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