Forget the Process: It's the Corporate Politics of iPhone Development That Best Explains It

Every company has people and a history. And they matter, however disruptive and forward-thinking the organization may be. JL

Dieter Bohn comments in The Verge:

The most important thing about that process isn't the process. It's the hidden rules and gotchas behind it.You have to understand Apple's resolve to keep a user-accessible file system away from iOS users. You have to know that at one point ringtones were Big Business and piracy was worrisome enough that the music industry forced Apple to do user-hostile things. You have to know that the iPhone was originally conceived as a satellite to the iTunes digital hub.
Recently, I decided to buy an iPhone 6S and turn on iMessage.1 iPhones are great! But in the process of setting it up, I ran into some hassles that reminded me that for all the advancements that Apple has made with iOS over the years, it still can feel like it's stuck in an old era of phones that were controlled by corporate politics. The iPhone is a computer, but sometimes it acts too much like a RAZR.

1. Because iMessage is such a good and compelling messaging feature, a lot of my friends and family use it and, I have discovered, are much more likely to talk to me when I also use it. I find this lock-in distressing, as it inserts a purchasing decision and platform theology into my personal relations. In order to have a better relationship with my family, I have to buy a particular phone. C'est la vie!

I am going to document the process that, in 2016, I went through to get my preferred ringtone on an iPhone. It is a story of complaints and gripes, yes, but it is also a story about why Apple's philosophy about how it thinks the "future of computing" should work keeps making the mistakes of the past. It's not just process, it's layers and layers of politics.

Ringtones, really?

After complaining on Twitter (which is what Twitter is for) about this situation, a bunch of people wondered why anybody even bothers with ringtones anymore. So here is a brief aside about my ringtone and why I care about it so much. You might actually be able to make the case that it is an illicit ringtone, even pirated. Except that it's the theme song for a TV show, and so I justify it by thinking of it as an audible advertisement for the FX network, so hopefully the copyright owners don't mind. It is, you see, the theme song for Archer.
Just listen to it: it's jaunty and happy; but also, underneath that, slightly ominous. Something dangerous is about to happen, but don't let it get you down because this music is fun! Thematically, it's perfect for somebody calling you — because going through the effort of an actual phone call in 2016 usually involves bad news.

Also, just sonically, it's great for a ringtone. It starts a little quiet, with a few different kinds of instruments hitting different pitches and notes to get your attention. but then, eight seconds in, the horns blare: pay attention, idiot, your phone is ringing.
Okay, aside over. Here's how to get a ringtone on your iPhone. It is a process that is appropriate for phones as they were designed and used in 2007, not 2016.

Step One: Try to buy it

There is a Preferred Way to get ringtones on an iPhone: buy them. The iTunes Store is still a Thing on the iPhone and you can still buy ringtones on it. So despite having my own MP3 of the theme song, I went to iTunes to see if an official ringtone was available. I instead discovered that I could only find cover versions. Some of them aren't terrible, but none of them are as good as the original. Does FX know that there are so many Archer theme song ringtones, each costing $1.29, and is it getting paid for them? I don't know, but I suspect not. Anyway, I wanted the real thing. Next step!

Step Two: Google

I'm aware enough of how the iOS ecosystem works that I knew I wouldn't be able to accomplish my goal by just poking around on the iPhone. For one thing, despite the fact that I have my MP3 stored on Dropbox, I also know that the iPhone doesn't have a user-accessible file system — so there's no place to just store that music file locally.
When I want this ringtone on an Android phone, I just download the file from Dropbox into the appropriate folder in Android, open up settings, and select it. Yes, I have to deal with a file system, but no, I don't need a fainting couch when that happens. Neither, I suspect, does anybody else.
Anyway, I knew what the process would be but I Googled it anyway, just to double check my assumptions. True story: there are a ton of articles from 2008 about iPhone ringtones, but not very many recent ones. Further proof that I'm old.

Step Three: Convert the file in iTunes

iTunes gets a very bad rap, and it deserves it. Nevertheless, I opened it up. Here is the easiest method for converting an MP3 file into a ringtone in iTunes. Note that this assumes the MP3 file is also trimmed to the precise portion of the song that you want.

1. Drag the file into your iTunes Library
2. Right-click it and click "convert to AAC"
3. Drag that AAC song out of iTunes and onto your desktop
4. Rename the file from "Archer.m4a" (for AAC) to "Archer.m4r" (which is a Very Special File Extension for ringtones)
5. Back in iTunes, delete the original MP3 file you just added and the AAC file you created, otherwise when you add your new Ringtone file it might not get recognized as a new file
6. Drag the "Archer.m4r" file into iTunes
7. Ensure that iTunes is set to sync ringtones to your iPhone
8. Sync your iPhone over USB

I find this eight-step process to be legitimately insane. It exists because Apple made a decision a long time ago that the iPhone should be made "simpler" in some very specific ways. You could argue that it's about locking things down. You could definitely argue that Apple is constrained by music industry interests and can't make the process for putting your own ringtones on a phone too simple or else it'll get into hot water with record labels.
But whatever the historical or philosophical reasons behind abstracting access to a file system and ringtones might be, that doesn't change the fact that this is a broken user experience.
And even if you accept this user experience, you have to trust that all eight of those steps go smoothly. For me (and for many people), they do not. Specifically, steps 7 and 8 went very, very badly.

Step 4: Head, meet desk

My brand new iPhone has synced to iTunes on my computer before. In fact, I restored it from a local iTunes-encrypted backup, which is usually way faster than an iCloud backup and tends to do a better job keeping app passwords intact so I don't have to re-enter a million of them on a new phone.
I mention this only because it's important context for understanding my rage when I clicked the "Sync Tones" checkbox and was presented with this screen:

Let us examine a few ways that this pop-up dialog in iTunes is wrong or hostile to the user:

1. My iPhone is synced to this iTunes library. In fact, I synced it literally seconds before I clicked the checkbox.
2. Uh, do I have another iTunes library on "dieter-macbook." Is that the current name of my computer? I just don't know without going and looking in arcane places.
3. Do I want to erase my iPhone? Hell no. That sounds like a great way to destroy an entire afternoon.
4. Why can't I can't sync my iPhone to different libraries anyway? I mean I know the answer, but the answer is related to iTunes being old — or the answer is that it's a way to prevent piracy. Either way, not my problem!
5. The fifth reason is so big I'm just going to end this list and tell you in a whole 'nother paragraph.

The worst thing about this dialog is that it is lying to you. Clicking "Erase and Sync" will not erase your iPhone. It will erase certain portions of your iPhone — namely the iTunes portion of it and possibly other music, movies, and TV shows you've synced. And yet, the button says "Erase and Sync," which is appropriately scary about erasing things, but inappropriately informative about what's getting erased.
What's more, I got this dialog literally the instant after I synced this iPhone to this very Mac. Or this very "iTunes Library." And yet, apparently it was synced to a different iTunes library. What is going on here?

What have we learned?

So that's the process for loading a bespoke ringtone on an iPhone in 2016. It's ridiculously annoying at best and totally broken at worst.
But the most important thing about that process isn't the process. It's the hidden rules and gotchas behind it. In order to get through this entire process without confusion, you have to do a bunch of Googling for answers. You end up on six-year-old message boards and reading articles written by robots.
You don't need to know the process — you need to know the politics
Most of all, you end up realizing that to fully understand what the iPhone is and how it works, you don't need to know the process — you need to know the politics. You have to understand Apple's adamantine resolve to keep a user-accessible file system away from iOS users. You have to know that at one point in time ringtones were Big Business and ringtone piracy was worrisome enough that the music industry forced Apple to do user-hostile things. You have to know that the iPhone was originally conceived as a satellite device to the iTunes digital hub and there are still vestiges of that philosophy hanging around.
Once you start looking for user experiences on the iPhone that are driven by politics, you start to see them everywhere. I could argue that there is a direct line from the tightly-controlled and carrier-captured Motorola RAZR to the "App Extensions" that Apple requires for inter-app communication.
That wouldn't necessarily be a fair argument. But having it would drive us deep into a debate about whether or not iOS is open enough for developers who want to create things that you would expect to be able to do on the platform that Tim Cook called the "future of personal computing."
I really enjoy that debate, and I care deeply about its outcome. But after dealing with the crufty corners of iOS last week, what I really want to know is how much of that debate is happening inside Apple.