Chosen Solution
So I’ve had my iPod 5th generation for a couple of years and suddenly the sad iPod icon showed up. I tried doing a lot of research on how to fix the issue, but i’ve had no luck at all. When I put the iPod into disk mode it says “do not disconnect” but it doesn’t show up in iTunes nor Disk Utility. I can hear the hard drive trying to spin inside of the iPod. But, when I put the iPod into disk mode, and instead of connecting it to a computer I connect it to a power supply, it just keeps saying “ok to disconnect” and it looks like it’s charging. I just don’t know what to do anymore.
Joe Yzaguirre, the very first thing I would try to do is to recover any files. Do this through your computer OS and not iTunes. Then I would check the hard drive. Place the iPod into diagnostics mode and see what result you get. For the how to, and what those results mean, check on here. It does sound like a bad HDD or HDD cable to me, but verify this first. If you are so inclined, you can also purchase an inexpensive USB to Zif adapter which will allow you to check the drive independently from your iPod. Hope this helps, good luck.
