Troublesome iPod

In an effort to get away from the shitstorm that is 2020 (COVID-19, major upsets in my personal life, etc), I decided to visit my mom, back in my hometown.

Dem boonies§

To frame things a bit, my mom lives a fair ways out from "town". This means that certain amenities that I've come to take for granted aren't available. Things like a truly high speed internet connection (I'm sorry, but DSL does not count any more), cellular reception, a coffee shop filled with cute baristas and college students...

I digress.

One key point is that the online world is not easily accessible when you take a few steps out of the cityverse. This also means that things like Spotify aren't really usable, especially for my mother, who's as far removed from a "tech wiz" as anyone I know.

But she does love her music.

And she has loved her iPods. A tiny device with one of the greatest navigation interfaces of all time (seriously, can we bring back the click wheel?), loads of storage space, loads of battery life, and loads of not needing an internet connection.

Like too many things in tech, they don't always age well. The iPod Classic my mom had been using for the past few years can barely hold a charge longer than 2-3 hours of playback time. Additionally, the data/charge port on the device1 can only do the latter. Plugging it into a laptop yielded zero device recognition, on either Windows or Linux.

So, the old device was kaput. No way to add music, no way to migrate said music to another device, nothing.

But, this didn't stop my mom from ordering a "new" iPod. Apparently, you can still get these things on Amazon2.

So, there we were with a new iPod to load up with music and a laptop that (very luckily) had pretty much every song my mom had on her old iPod. +1 for coincidental backups.

So you want to transfer some files?§

It being 2020, and iPod Classics having ended their official manufacturing run 10 years ago, I thought - "it has to be possible to upload music to these things without iTunes, right?" I mean, we had a Linux laptop that I brought and her Windows laptop for optimal spread of operating system support. Surely there must be some free software that's been written that easily imports music from a folder into the iPod Classic!

Boy, was I wrong.

I tried:

  1. aTunes
  2. YamiPod
  3. Manual workarounds like revealing hidden folders in Windows, navigating into the iPod's hidden Music folder, and drag/dropping some files in.
  4. A fleet of other software all based around shared libraries used by YamiPod.

But nooooooo. Apple builds such brilliant hardware that something that should be as simple as copying a bunch of MP3 files into a folder isn't even possible. In fact, it's actively disallowed.

This isn't really news to anyone. Apple created the greatest MP3 player in the world (and possibly ever), but everyone who got one hated one thing about it - having to use iTunes to manage all of their music. It was slow, it locked down a device to a particular computer, music couldn't be easily shared with friends, etc.

All around iTunes was a total regression in user experience, which juxtaposed so very shockingly with the excellent UX that the iPod Classic offered (I mean that click wheel).

And here we are 10 years later, and we're still back at square one - use iTunes.

To be fair, there are a stupidly large number of paid spyware apps that claim to handle iPod Classics with zero problem. And I believe them - we as a society have had a very very long time to nail down a 10 year old piece of hardware. But we seem to have given up.

Or at least I've given up.

We downloaded iTunes, installed it, and I drag/dropped 110GB+ of music onto the device and away we went.


But I learned something. I learned something about myself and Apple. I learned that Apple will actively create consumer unfriendly software. And I learned that I don't want to deal with its bullshit any more. Just give me an MP3 player with an SD card slot and I'm good.

Oh look - they do exist

And of course, it looks like an Apple Watch...


  1. Those old wide + flat connectors from back in the day before Apple made 2-3 more connectors and now everything requires a damn dongle.
  2. Although they aren't nearly as cheap as they should be.