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.