iPod 4th gen (Clickwheel) needs iPod Support on iTunes but it's not installing?
Hi folks! I got an old fourth generation iPod (clickwheel) from a family friend that hasn't been used in two decades, and I was so happy to see it could still charge up and be used. I was hoping to transfer my music library onto it, but when I turned on iTunes on my laptop (Windows) and connected the iPod, I got a pop-up notification saying I needed additional software. I agreed to install, but this is what the top of the window has looked like for the past hour:
It hasn't given me any updates regarding timing or progress. The iPod just has a message on its screen saying "Do not disconnect". I considered it might be an iTunes problem since I'm pretty sure I have the latest version and trying to connect it to a relatively old piece of tech, but I don't know how to go about downloading an older version (would I have to uninstall the current version? which version would be best from what's available here?).
Not sure how long I'll be here stuck in installation purgatory or what next steps are, so any advice would be helpful.
Posted Mar 1, 2026, 1:46 AM UTC