iTunes is the glue of Apple’s software universe: It connects the company’s phones and tablets, desktops and laptops, and online media store and streaming service. It is also, in the inimitable judgement of the indie iOS developer Marco Arment, “a toxic hellstew.”

I agree: It’s why I wrote about how poorly iTunes performs for classical music listeners and, really, for anyone with a large music library.

But it’s worth spending time on iTunes’s specific design problems, which surpass those raised by managing a music library or listening to a specific genre. Toxic hellstew it may be, a new version of iTunes points at what kinds of technology are allowed to come out of Apple. Apple is the most valuable company in the world and an organization hailed for its good design. Why does iTunes fail at what it sets out to do?

Arment blames its failures on Apple’s decision to cram too many different features into one piece of software. He believes the company should have discontinued iTunes, its media management service, and rolled out a new Apple Music app. (Arment doesn’t say whether this new app would also play MP3s.)

iTunes’s user interface follows from this poor strategy, too. Its “design is horrible […] not because it has bad designers, but because they’ve been given an impossible task: cramming way too much functionality into a single app while also making it look ‘clean,’” writes Arment.

Does this kind of failure—call it institutional cruft—appear in iTunes? I think absolutely. Let’s look at the app.

The navigation bar lets users navigate between “My Music,” “Playlists,” “New,” and more.

Look specifically at the horizontal navigation bar, which sits below the scrolling song title and the main window content. Because iTunes inserts a forward and back button to the far left in Apple Music and the iTunes Store, menu options in the bar will sometimes change location after you click them.

When navigating Apple Music, above, iTunes inserts a forward and back button. When navigating a user’s music library, as below, it doesn’t—which moves all the menu options around.

So if you’re in your own iTunes Library, then click on “For You,” you’ll find the entire navigation bar has shifted under your mouse: Your mouse is now hovering over “Playlists,” as the software has inserted forward and back buttons on the far left.

From a user-interface perspective, this doesn’t make any sense. Users expect that menu items in a navigation bar won’t change their location after they click on them. When you click on a bookmark in your browser’s navigation bar, all the bookmarks don’t suddenly shift around.

This messiness is as institutionally crufty as they come. With Apple Music, iTunes’s designers had to find a way to navigate a web-y, browser-like environment in the main content area, and that requires back and forward buttons. In a music library, though, the content area also needed to scroll through a stable list of MP3s. The designers couldn’t move the forward and backward bar any higher, into the playback area, because the logic of that area is that it’s all music control—and, besides, there’s already a forward-arrow and backward-arrow in there, on the left, which control tracks.

iTunes had to serve two different purposes, so the forward and back buttons had to go in the navigation bar.

Keep looking at that bar, though, and I think a different kind of user-interface failure emerges: the kind that results from poor decisions. In other words, I wonder if iTunes’s failures can’t just be entirely blamed on Apple’s crufty, legacy obligations, but on a deeper inattentiveness in the company.

Focusing on that bar, here’s what sticks out to me: iTunes can’t decide how to address the user. The user’s MP3 library sits behind the menu title “My Music.” But Apple Music’s recommendation interface is accessed by clicking on “For You.”

Is the user “my” or “your”? Is iTunes an extension of the user or is it in conversation with them? Designers have thought about these issues before; Yahoo’s own interface guide suggests:

Labeling stuff with ‘My’ imitates the point of view of the user. It is as if the user has printed out labels and stuck them to various objects: My Lunch, My Desk, My Red Stapler. Except the user hasn't done this; you (the site) did it for them.

Labeling stuff with ‘Your’ instead reinforces the conversational dialogue. It is how another human being might address you when talking about your stuff. Even with MySpace, people say things like ‘I saw what you put on your MySpace.’

I’ve also seen financial apps use “your,” because a bank saying “my money” is a little weird. That $200 in my savings account isn’t yours, dude.

Which is all to say that this is a solved problem. People have considered this, set precedents, and shipped software, yet here comes iTunes, from the most design-friendly company in the world, disregarding them. And this isn’t the only odd microcopy choice: Apple Music, the company’s entire streaming archive of recorded music, is located at the menu item labeled “New.” That’s partly where Apple promotes new releases in an iTunes Music Store-like interface, but it’s also where searching for a record in Apple Music will send you. Nearly everything in Apple Music—from a Thelonious Monk record from 1963 to a CHVRCHES single released last week—is conceptually located in “New.”

These recordings are almost 80 years old, but, because they’re in Apple Music, iTunes locates them in “New” in the navigation bar—because that’s where almost all of iTunes Music is.

It doesn’t have to be this way. “For You” could be titled “Recommendations,” resolving the discrepancy.

It’s possible that these mistakes originated in institutional politics: Maybe Jimmy Iovine insisted, required, would get up right now and walk away from this stupid white plastic table if the recommendation system was called anything other than “For You.” (Apple did not respond to my interview requests.)

But I doubt it. It strikes me as an inferior design decision, arising from inattention. It’s a minor problem, sure, and there are more pressing ones in the software. I have seen Apple Music streams drop mid-play; other users have lost music with iTunes Match. But as Apple is never far from telling us, music is something about which they’re “profoundly passionate,” “a force that’s driven and inspired us from day one.” The point of Apple’s design ethos is that making things a little better than they have to be, for the average user, is a form of respect. I hope that as Apple becomes less of a media-tech company and more of a jewelry maker, its leaders remember that.