HT201625: Manage and back up your iTunes media library
Learn about Manage and back up your iTunes media library
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Helpful answers
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Aug 21, 2015 3:47 AM in response to Alan2770by turingtest2,First see Backup your iTunes for Windows library with SyncToy.
Deletes the song from the device, or the library?
Is it still present in the media folder?
Have you enabled iCloud Music library?
Do you have any iOS devices in addition to the iPod classic?
Are you manually managing the device or syncing it?
Do you have the option "Sync higher bit rate songs to xxx AAC" enabled?
tt2