I know you are having trouble in transferring MP3 songs to your Chromebook to the iPod Classic. Here are a few suggestions to test:
- Check that you're iPod classic has been formatted to FAT32 as well as exFAT. You can verify the formatting for your iPod classic through connecting it to a computer and then opening Disk Utility. If the iPod classic was formatted to other file systems, you will need to change it to a different format.
- You can try using an alternative USB cable. In some cases, a damaged USB cable could prevent data from being properly transferred.
- Try trying to reboot your Chromebook as well as restarting your iPod Classic. Sometimes, a quick restart will fix small issues.
- If you're still struggling trying a different application for file transfer. A variety of file transfer software is accessible to select one that is compatible with both your Chromebook and also your iPod traditional.