Around 10 years ago, exasperated by a roommate’s tech woes, I convinced the guy to dump his Windows laptop for a Macbook, promising that if he’d switch, I’d be his tech support for life. At that point, I’d been an Apple user for six years, and had showed him over and over again how “it just works” was just fact. I never had a virus to speak of, never had a problem with an audio or video card, and had never been personally crippled by a blue screen of death.

But in hindsight, after a decade of phone calls, emails, walk-throughs, and being treated like a walking, talking FAQ, I’m admitting defeat. Converting him and many other people to Apple may have been a bad idea. Of course I’m saying this after his latest question—“How do I put music on my iPhone?”—nearly made me throw my iPhone at the wall, a heck of a way to end the call.

Don’t blame my exhaustion on my friend’s lack of technological know-how or my own dwindling patience. Blame iTunes. Once the ultimate in music file management and the centerpiece to Apple’s financial turnaround, this program has evolved from a simple, dependable music player into the biggest example of bloatware in computers today. But why mince words? I hate iTunes. And I think Apple does, too.

To figure out where this once-stellar program went so terribly wrong, you have to look at how it got to where it is today.

To figure out where this once-stellar program went so terribly wrong, you have to look at how it got to where it is today. Billed as a digital jukebox, iTunes launched in January 2001 at Macworld in San Francisco. “Apple has done what Apple does best—make complex applications easy, and make them even more powerful in the process,” said Apple CEO Steve Jobs at the time. Just nine months later iTunes 2 came out, landing alongside the iPod, the MP3 player that forever changed music.

iTunes 3 came and went, and in April 2003, iTunes 4 landed as a monumental upgrade, introducing the iTunes Music Store, as well as rolling out video support and Windows computer compatibility. The importance of these improvements can’t be overstated for Apple’s financial success, as well as for the evolution of digital media at large. With iTunes 4, millions of people were suddenly granted instantaneous access to digital downloads on demand. Apple famously sold 1 million songs in the first week, and 25 million by the end of the year. People were buying music again, no longer stealing it from the web. The Apple music ecosystem worked well, and everyone was happy. (Well, everyone except for Kid Rock.)

But as Big Download got rolling, so too did iTunes. Movies, television shows, and music videos arrived for sale with iTunes 6 in 2005, and with them came new tabs in the program for managing that content on devices. But as Apple pushed out new generations and models of iPods, iTunes also became a device manager—and not just for Steve Jobs’ gizmos. An awkward relationship between Apple and Motorola resulted in ROKR, SLVR, and RAZR, the Huey, Dewey, and Louie of music phones, and those too were administered by the jukebox app. Nike+ interacted with iTunes and iPod Nanos. AirPlay connectivity was rolled into the application, and compatible speakers could connect to the program. Front Row, a slick media management skin, even premiered—just long enough to get pushed to the background when Apple TV (also an iTunes joint) appeared with iTunes 7.

So in just a few generations, iTunes went from being a svelte piece of software to an octopus of an application—and with that, an array of problems began popping up. iTunes 7, for instance, saw 18 updates in less than 12 months. Likewise, iTunes 10 (with Ping!) had 19 updates in a year. iTunes 11, meanwhile, needed 17 patches in its 11 month life. On the bright side, things are looking better for iTunes 12—with only three releases since its rollout in October—but the launch of Apple Music could easily upend that. So, as we all laugh at Flash for its seemingly bi-weekly parade of upgrade prompts, it’s fair to ask if iTunes is any better.

All this history sidesteps the injection of the App Store into iTunes. With the launch of iOS 2, iPhone owners needed somewhere to download their various digital goodies from, and someone in Cupertino thought it would be a great idea to make iTunes that place. In the end, this decision will prove to be a fatal mistake for iTunes because it didn’t merely add another category of media to the already chubby program, it actually introduced a whole new realm of computing. And the effects of apps in iTunes have rippled across Apple’s Mac OS, from the small and annoying (like how clicking on an app’s webpage springboards iTunes to open, an undesirable effect that can take minutes to unfurl because the program now opens like a rusty zipper) to the potentially problematic (iTunes glacial performance has to be pushing casual listeners away from their owned digital media towards more nimble music experiences like Pandora and Spotify—I know it’s made me quit opening iTunes, listening to my music, and potentially buying more).

Apple Music’s launch marks a last ditch effort by the company to stay in the game.

And though Apple has pocketed billions during the swelling of iTunes, it might not work out so well for Apple in the end. Apple very nearly missed the boat as streaming music has supplanted selling it. Apple Music’s launch marks a last ditch effort by the company to stay in the game. They may never reach the music download revenue that they once did, but then again, neither will anyone else. And since the money has moved from owning to listening, the company is trying its hardest to make sure they can capture as much of that transitioning market as they can.

And this is essential for Apple because while music may not earn the company much money, it makes for great marketing. For instance, last year Apple’s gross income was just over $70 billion. During that time, iTunes generated $10.2 billion in net sales, despite a decline in digital music purchases. Though the company doesn’t provide a breakdown of apps versus media sales, the company noted in its 2014 annual report that iOS software has taken over what’s really driving iTunes now.

By comparison, hardware brought in more than a $158 billion dollars. While margins vary between media, software, and hardware (it even differs for iPhones, iPads, Macs, and iPods), using napkin math on Apple’s 70/30 profit-sharing split would ultimately push roughly $7 billion in profit from iTunes toward the bottom line. From there, keep in mind that apps are king, and you could estimate a modest $3.5 billion (if that) comes from music sales. To most companies, it’s not chump change, but to Apple it’s only 5% (again, if that) of their haul.

But this chunk of change is even more valuable when you turn it into a marketing machine. Whether it’s by squabbling with Taylor Swift or making up with Eminem, music is what keeps Apple socially relevant. And just ask Samsung—that’s something that money can’t buy. Because the real story behind Apple’s success isn’t so much music as it is stuffing hard drives past their capacity. Filling the storage space on Apple devices is key to getting consumers to buy new ones. How many times have you heard someone say that they need a new phone or laptop because their current one was full?

With the slow death of iTunes and the decline of purchased media, Apple has had to find new ways to make that happen. Doubling the size limit on apps from two to four gigabytes certainly helped, as did bulking up the size of iOS itself (temporarily crippling many eight gigabyte iPhones, a black eye for Apple). What’s stuffing phones, tablets, and computers fastest is user-generated media—photos and videos. As many a parent will attest, no gigabytes are enough to satisfy the appetite of Apple’s great iPhone cameras. But one problem for Apple is that this kind of media doesn’t pay. That is until the company launched its iCloud Photo Library, which guarantees the company a subscription revenue stream from people who have sign up. And why wouldn’t they? By putting your photos in the cloud, they remain safe and can allow you to fill your phone with more apps and media (for the few who still actually buy it).

Apple’s new music offering will show up in an updated version of—you guessed it—iTunes.

Which comes to this week’s news, the release of Apple Music. Free to stream for the first three months, and easy enough to get hooked on after that, on the desktop, Apple’s new music offering will show up in an updated version of—you guessed it—iTunes. Never mind that it will appear on the Music app on iOS (or that the Mac OS has aped Apple’s handheld apps with Mail, Maps, Photos, etc. appearing on computers). Instead, Apple is just stuffing something else into iTunes. Again.

So open up iTunes, if you can, and enjoy Apple Music. And while you’re in there, try to quickly put some of your old tracks onto your iPhone. In trying to tell my friend how to do it, I didn’t know what to say. Yes, I know there are a variety of ways to load up your library, but the guy has a legitimate gripe. He bought some CDs in the 90s, ripped them, and wanted to just pop a couple tracks onto his new phone—how hard could that be? If it “just worked,” he shouldn’t have to ask how to do it. But somewhere along the way, iTunes stopped just working. Instead, it started selling.

Ultimately, I told him to do what everyone else is doing—sign up for Spotify.