this post was submitted on 28 Nov 2023
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Unfortunately Apple seems to be actively working to make sure that the only way an iPod can be loaded with music is by using iTunes which is only supported on Mac or Windows.
You have a few of options on how to move forward:
1: Make a Windows virtual machine, install iTunes onto it and pass the iPod though to the VM.
2: Install Rockbox (if able) onto the device to enable it to act as a USB mass storage device allowing drag n drop loading of music.
3: Sell the iPod and get one of the many different digital audio players available on the market as most are OS agnostic (they show up as a USB mass storage device) and most use MicroSD cards to store the music meaning you can move the card to a new player as you upgrade later (so you are not locked to one vendor).
Wanted to say that I've used Rockbox on an old ipod classic with much success. Would recommend. You can even install user created apple-ipod-like themes to get closer to the original look N feel
Thanks for the the tjps but they all don't look likely they would run.
Did you adjust the resources given to the VM?
I know with Oracle Virtualbox it defaults to like 1 processor core and 500mb of ram for a VM.