If you are using an iPod, you can consider this way here to transfer non-purchased music from iPod to iTunes for free. But it’s more complicated, and it’s not available for iPhone and iPad. If you are using a Mac, this way is not suitable for you.
Step 1. Connect your iPod to computer with a USB cable.
Step 2. Open up the “My Computer” window andyour iPod will be shown up there.
Step 3. From the menu bar, click on “Folder Options” followed by “View”. Under “Advanced Settings”, make sure that “Show hidden files and folders” is checked.
Step 4. Head back to the “My Computer” menu and double-click on your iPod to open up its files.
Step 5. Locate and enter the “iPod_Control” folder, folder by the “Music” folder. Copy this folder to your desktop.
Step 6. Open iTunes, click on “File > Add Folder to Library”.
Step 7. Head to your desktop and select the music folder which you just copied. Click “Open”. After a few minutes, you will be able to find your iPod’s music in your iTunes library.
Step 8. Lastly, head to the “Edit > Preferences” menu and click on the “Advanced” tab. Check the box next to “Keep iTunes Media folder organized”.
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