Herr Bischoff

When Spotify Uploads to Apple Watch Do Not Work

I’ve spent the whole of today trying to troubleshoot why uploading tracks to my Apple Watch did not work. No matter what I did, the process stalled on Apple Watch, being stuck at “1 of 50 downloading”, never proceeding beyond this initial state.

After having spent two hours with their Twitter support (@SpotifyCares — and yes, they do not offer support via email or any other reasonable venue), a fully restored iPhone and Apple Watch in hand but still not an inch closer to resolving it, I tried logging the DNS queries.

My Pihole DNS server blocked several connections of the usual smattering of tracking and telemetry crapola:


However, I also spotted an interesting outlier


which looked suspiciously like a domain transporting legitimate service traffic. So I white-listed it temporarily, just in case. And what do you know: the Apple Watch uploads started immediately. They are rather slow but they work.

I wish Spotify was more adept at resolving technical issues and used less invasive tracking. Whenever you open your Spotify app, no less than four different companies are contacted, collecting data. Every. Single. Time. And while we’re on the topic: the fact that playlists are public by default (a default you cannot change) and everyone can stalk the artists you follow is rather off-putting to me.

Anyway, if you’re having issues with this, before you try reinstalling anything, check if the network you’re using is filtering DNS queries — and if so, that the respective domain is white-listed. When using Pihole, it’s as easy as:

pihole -w audio-ak-spotify-com.akamaized.net