QUESTION: I have an older model iPod (with a wheel). The computer with which it was originally set up is no longer viable, although I do have the iTunes backed up on a portable drive. Unfortunately, the iPod will not recognize the portable, and if I try to sync with an updated iTunes on my current laptop, I’ll lose all my music. Is there any way to retrieve the music off of my iPod and transfer it to my laptop outside of iTunes? I have more than 1400 songs which I can only listen to on the iPod, and if it crashes, I’m up a creek. Thanks. – Lori W from Valley, Alabama
The first solution is to copy your iTunes music folder from your portable drive over to your new laptop. This assumes your backup is not compressed and contains the correct folder structure that iTunes expects. If you get lost in any of the steps I am about to describe, you may have to skip to Solution 2.
Start by browsing the folder structure of your portable drive. In the Music folder, look for and open the iTunes folder. Under iTunes look for and open the iTunes Media folder. Finally, locate the Music folder.
Right-click with your mouse on the Music folder and then left click on Copy from the menu that appears.
Now navigate to the same exact structure on your laptop. As a refresher, the path is Music\iTunes\iTunes Media. You should be viewing the Music folder not looking inside of the folder.
Right-click with your mouse on a blank area of the window and choose Paste from the menu that appears.
This should copy of all your music from your portable drive back to your laptop. When it is complete, you should be able to open iTunes and see all of your music there.
Solution 2 involves directly copying the music from your iPod to your new laptop. Since I’m not a big fan of re-inventing the wheel, I’m going to link to a wikiHow page that already describes this process step by step: How to Copy Music from Your iPod to Your Computer
Good luck! I hope one of these solutions works for you.