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I've formatted my computer recently (Windows 8). For some reason, I couldn't import my backed up .itl file.

I've decided it would be less trouble if I just made a new library and erased and synced the current one in my iPod. However, it tries to sync without erasing, which results in an error: Cannot sync because at least 18 GB of free space is required.

This had happened the last time as well. I'd resolved to erase the music on my iPod through its settings. It had erased it, but leaving the song names, etc. there. Although there wasn't any music left in it, iTunes perceived it to be full, and I could still see the song names in the iPod, but I couldn't play them.

I ended up having to restore the iPod, losing all app data (high scores that are not synced to gamecenter, preferences, etc.). I really don't want to go down that road again.

Why is nothing going as expected in iTunes? What is the safest way: the way in which I save most of my data?

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Backup your iPod, then factory reset it, the restore the backup you made. – Ramhound Sep 6 '13 at 18:35
That erases some of the app data. That's what I did the last time. – sodiumnitrate Sep 7 '13 at 15:47
up vote 1 down vote accepted

Uncheck Sync Music, hit apply. This erases all the music successfully. Then, re-check Sync Music, and hit apply again. Wait for files to be transferred.

Since all the files have to be transferred, it lasts longer than it would if erase and sync had worked.

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