Hello there dtneese,
It sounds like you are getting an error message 1439 when you are trying to restore your iPod Classic. I recommend the troubleshooting steps from the article named:
iPod: Can't restore or update in iTunes with error 1415, 1417, 1418, 1428, 1429, 1430, 1436, or 1439
- Disconnect and reconnect your iPod to iTunes and restore or update the iPod.
- Restart your computer and restore or update the iPod.
- Connect your iPod to a different USB port (a USB 2.0 port if possible) and restore or update the iPod. For Windows computers, follow these steps to identify USB 2.0 ports.
- Disconnect any third-party USB devices from your computer. You don't need to remove your keyboard or mouse. Then, restore or update the iPod.
- Update iTunes and restore or update the iPod.
- Use a different user account on your computer to restore or update the iPod. For example, create a new test user account on the computer with admin rights and iTunes and restore or update the iPod.
- Turn off Disk Use on your iPod and restore or update the iPod.
- Turn on Disk Use on your iPod and restore or update the iPod.
- Reregister ".dll" files by using these steps under "Solution 1."
- Update or reinstall your Windows USB drivers using these steps under "iPod only: Updating, or in some cases reinstalling, the drivers for your computer's USB interface may resolve this issue."
- If you use third-party security software, you might need to update, disable, or uninstall your security software temporarily.
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