HT201625: Manage and back up your iTunes media library
Learn about Manage and back up your iTunes media library
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Apr 20, 2016 7:31 PM in response to lolaswolfby Kenichi Watanabe,★HelpfulIf you "restored" your iTunes library by adding your songs (and other content) to a new iTunes library (instead of restoring the complete iTunes library from a backup), your current iTunes library is treated as a different iTunes library by the iPod. iPods can only use automatic syncing with one iTunes library at a time. If you set up syncing with your current iTunes library, the iPod's existing content (from the old iTunes library) is erased and replaced with content from your current iTunes library. Any songs on the iPod that are not on your current iTunes library will be lost.
By design, iTunes syncing is generally in one direction only, from iTunes library to iPod. You cannot use iTunes to transfer song files from iPod to computer (except for songs purchased from the iTunes Store). However, there are third-party methods and utilities that can transfer from iPod to computer. If you do an Internet search on something like "ipod music transfer," you should get some links (including an article by CNET on the topic).
Once the song files are on your computer's drive, add them to your current iTunes library. After confirming your iTunes library has all of your songs, you can set up syncing with the iPod.