Changing music services is a miserable experience

Why does changing streaming services, or even music player software, have to be an experience so hostile?


The first time I moved from one “music service” to another was when I moved from Winamp to iTunes. Heresy, I know, but my music collection was growing fast and I wanted an easy way to manage all the files, and iTunes provided that by renaming and creating folders automatically. It was great and, despite missing tags and incomplete discographies, I was pretty happy with it. When I bought an iPod a few years later, it was even greater.

This was on Windows, by the way. In Brazil, Apple computers were (and still are) rich people’s products.

So, everything was working fine until a few years later, when iTunes suddenly corrupted and lost all of the playlists I’d been building over the last, I don’t know, 5 years or so. At the time, Spotify was still a new thing — smartphones were just starting out too — and it seemed like a good idea, as it synced with the iPod and allowed you to mix your own mp3 with the streaming songs. It was my first move to a streaming platform, and it was relatively painless because I had to build my playlists from scratch anyway.

When the iPod support was dropped, I didn’t mind, the streaming playlists were “more complete” and easier to handle than trying to organize. Playing local files is still available, but the feature now lives separately from the streaming songs, so that doesn’t matter that much.

Anyway, so things went up until some years ago, when the Spotify CEO started acting as an asshole towards musicians, especially after dropping how much each stream paid to them. I decided it was time to test new waters and, from the services available, I moved to Tidal. I had to use a 3rd-party tool to move my playlists from Spotify, since none of the services allowed to export/import playlists, which was not that great: many songs weren’t transferred because they weren’t available in this new streaming service, while some others were the wrong versions of a different album. It was somewhat annoying but easy to fix by hand, over time.

Tidal worked ok but, a couple of years later, I found out about Qobuz, which is the streaming service that pays musicians the most. It also sells digital albums, which is a neat feature that only Apple took advantage of. “Great,” I thought, “I’m going to build my digital library up again”. Except that it actually didn’t sell digital albums in my region, and it had even less songs from the less-popular artists that I like. And, again I had to use a 3rd-party service to transfer playlists, and again there were some errors among the songs the service had.

After around, I don’t know, 1 year or so, I had to save some money due to unforeseen circumstances, so decided to cut every monthly service I wasn’t using or wasn’t satisfied with, and Qobuz was among them. This was in early 2024, already. To keep listening to music, I searched for easy-to-set-up home alternatives and found out about Plex.

Plex is great: it scans your library and, through a companion app, allows you to listen to your music — as long as your PC with the music files is powered on and connected to the internet. It took many days for me to organize my collection, which I had been neglecting for years. Now, with metadata applied, albums I didn’t really like deleted, and a whole new playlist I made by hand, it felt like it was my definitive solution. And it was.

The issue, though, is that Plex works best if you have a throwaway PC lying around, with low power consumption, that you can use as a media server, otherwise it becomes inconvenient. Still, it was the best solution so far, and I was pretty happy with it… until I learned, this week, that Apple Music has something called “Sync Library”, in which they host your files on their cloud and play them together with the music they offer on their streaming service, seamlessly. Considering they also sell digital albums, and this time the service was available to me, it became very enticing.

And so it goes my saga now, trying to make Apple Music sync with my local files. It’s been pretty buggy on Windows but it worked ok on Mac. However, I found out that Plex doesn’t export playlists, and the only way to transfer them to Apple Music was using a 3rd-party service. Which, as predicted, doesn’t work as expected.

I feel like I’m going crazy with this because, in the space of 10 years, we lost the ability to simply move our music library around. Even Plex, which plays your local library, doesn’t have this basic feature. It also can’t import playlists, which is absurd. Funny enough, Apple Music can import and export playlists. It feels like the world is upside down.

Now it’s understandable then why so many people, especially those who didn’t build their digital library over the years, are so resistant to changing services: the whole thing is completely hostile to user agency: every one of these services lock the user in their environment and do their best to not let them get out, making everything as inconvenient as possible.

The irony of it all, for me at least, is that I’m not only returning to an Apple product that was responsible for throwing me towards streaming services — after all, Apple Music is the successor of iTunes, the thing that corrupted my playlists and prompted my move to Spotify — but they also seem to be the only company that allows you to mix local files with streaming songs and import/export playlists whenever you like. Even so, I lost my whole day trying to set up the Sync Library and went through a lot of trouble doing so.

I just finished running beets, which is an open-source music library tagger-organizer — that runs on the command line, which I hate to use, but that’s the price to pay — and I’m making Apple Music scan all the files again. Annoying, but there was a lot of wrong stuff in my library and, hopefully, I won’t have to touch them again for the next 10 years or so.

In the end, it’s funny how, as technology evolved, some things got worse for the end-user. I wonder how many young people nowadays know that, in the past, you could just carry your digital files around and play them on whatever device or digital music player you wanted.

I’ll tell you, I’m one step closer to just resurrecting my iPod and being done with all of this.

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