I can't get my classic iPod to sync with iTunes

See Sync your iPhone, iPad, or iPod touch with iTunes on your computer using USB - Apple Support.

Select the device, select the music tab within, chose what syncs, acknowledge the erase and sync warning, and let it sync your new list to it replacing what was already there.

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If there is media on the device that isn't in your library start with Recover media from an iPod.

Then see Sync your iPhone, iPad, or iPod touch with iTunes on your computer using USB - Apple Support.

What happens when you try to add content to the iPod?

tt2

Start with Recover media from an iPod.

When iTunes syncs that process generally means copy from the computer to the device, and remove anything on the device that isn't in your library. A restore on its own wipes the content from the device. From the sound of things you don't want to do either until you have retrieved the content that is on the device and not stored anywhere else. If you only have content purchased from the iTunes Store which you have redownloaded then there might still be ratings, play counts, or playlists that you can reclaim. You shouldn't sync or restore your device until you've taken that opportunity.

tt2

You're welcome. 🙂

tt2