I'm not sure how to do what you're looking for but you can install rockbox on the iPod and then just copy the music files over normally. That's what I've done and it works fine on Fedora.
this post was submitted on 24 Sep 2023
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As others have said there are a couple of options that may or may not work as Apple loves to make sure that their products only work with their software and a lot of them haven't been updated in years.
For ease of use you can install Rockbox on a good number of iPod devices, that will allow you to drag and drop music onto the device without having to use software to load the music.
If you are wanting an even easier option, you could sell your iPod and get one of the many different Digital audio player options that use microSD cards to store the music files allowing for ease of storage upgrades, ease of moving to a new device and being OS agnostic as they show up as a USB mass storage device.
I use a Fiio M7 as my daily driver with either a set of Jade audio EW1 TWS earphones or FiiO JH3 IEM's & I have an older Fiio X3 2gen connected up to a dock for playing music in my living room.
I started down this path after discovering that iTunes was flagging some of my music that I ripped from my own CDs or my dad's old records (that I now own). It shows on the iPod as "not available in this region" despite purchasing the physical CD from the record store across town!
The iPod is used 99% of the time in my car hooked to the radio, but I'll bring it into the office from time to time. I've been thinking to build something with a raspberry pi and big SD or SSD so that it shows up on my home WiFi when I park and I can syncthing or drag and drop music, but I don't have a lot of time to play. The iPod was a Xmas gift from my dad and (I know it's stupid) but I want to keep using it if I can.
Rockbox is all well and good until you realize your car's stereo doesn't recognize your iPod Classic as a music player anymore. Hours of forum rabbit holes later: turns out it's special firnware that Rockbox can't access, and probably won't ever be able to (unless apple voluntarily forfeits some encryption keys).
Like every other DAP, Rockbox gets your iPod recognized as a usb storage device by most vehicles. For the stereos I've used, this is a headache because they needed to index the entire filesystem at an agonizingly slow bandwidth... every time I started the car or had unplugged the iPod. One car slowly gave access to songs as they were discovered, gradually revealing the files to you over time, the other just displayed a message until completed (which hasn't ever happened, even on hour+ car rides). The same things occured with my Onkyo DP-X1, except that indexing would finish within my lifetime.
It was easiest just to use the 3.5mm jack for the car stereo tho, due to the indexing being required every goddamn time the car turned off or the player got unplugged. Which is a shame, bc my stereo may be stock, but they are quite nice and expensive DAPs (i even tricked the iPod out with an iFlash for SD card capabilities and a custom shell) and should be able to stream digital audio over USB.
There used to be the gtkpod project, but it's now probably unmaintained. Might be useful though
They mentioned GTKpod in the question
Rhythmbox maybe? It seems like a bunch of options use(d) the same sync library.
Disclaimer: I never had much luck either.
You know, I want something like this for my (Android) phone. I use SyncThing, but managing individual songa or albums through it is a pain. I want a tool where I can easily select which music gets synced to my phone, and which automatically syncs back all music I put on my phone.
I don't need the 13 hours of Christmas music on my phone, but I often acquire new music from my phone.
I'd love to hear of a good tool for music management; iTunes did a really good job of this.
YouTube Music allows you to upload up to 20,000 tracks to your personal storage for free. And then you can just pre-download anything you want or you have anytime access to just stream your whole library, without the need to preload your device as if it were 2003.
I used to do this! I mostly self-host stuff now, and do have a streaming music server. Streaming doesn't work in many situations - backpacking, airplanes, etc., and it's nice to have music on my device without needing internet.
Let me offer another thought, if you are literally hanging on to windows for this, you could set up a VM in linux for this task. This is how I manage win only apps like my security client (camera vms). You have a license for windows, make it more useful. (and no rebooting to swap!)
Or, a little more controversial, choose another player instead of Apple ipod. Plenty alternates that just work with linux.
I used to have an ipod 20 years ago, and there was a linux "itunes" application, but I doubt its still maintained, or apple has made it impossible for 3rd parties to manage an ipod.
I have a windows VM for a couple of other applications but iTunes wouldn't detect the device was plugged in inside the VM. This was several years ago and maybe the VM landscape has changed. I could try it again.
I just used a vm to restore my ipod yesterday. Simple Win7 VM worked like a charm. Just had to allow the usb passthrough in devices->usb. This is using virtualbox
Too bad Apple has abandoned them all at this point, even the 7th Gen Touch.
Ive been using rhythmbox. Its not perfect but it works.
Honestly, I would sell the iPod and get a modern player that has an SD slot or is known to work with Linux.