Marco Arment on iTunes:

iTunes is designed by the Junk Drawer Method: when enough cruft has built up that somebody tells the team to redesign it, while also adding and heavily promoting these great new features in the UI that are really important to the company’s other interests and are absolutely non-negotiable, the only thing they can really do is hide all of the old complexity in new places.

With the introduction of Apple Music, Apple confusingly introduced a confusing service backed by the iTunes Store that’s confusingly integrated into iTunes and the iOS Music app (don’t even get me started on that) and partially, maybe, mostly replaces the also very confusing and historically unreliable iTunes Match.

So iTunes is a toxic hellstew of technical cruft and a toxic hellstew of UI design, in the middle of a transition between two partly redundant cloud services, both of which are confusing and vague to most people about which songs of theirs are in the cloud, which are safe to delete, and which ones they actually have.

Hard to argue with this take. Apple clearly has both an engineering problem and a PR problem. They’ve also got a showdown coming up with Spotify. They’ve got about two months to go in the first wave of 3 months of free service, when customers will be asked to plunk down actual cash for the privilege of continuing to use Apple Music.

More important than cash, though, is asking users to trust Apple with their existing libraries. And there’s an easy fix for that problem. As Jim learned in his Nightmare post, back up your library before you let Apple Music get its hands on it.

Backups aside, Apple and the iTunes team appear to have their work cut out for them.