Though he only writes a major story every year or two, for the last decade and a half John Siracusa has built a reputation as one of Apple’s most influential critics. When he does publish a piece, it’s a 25,000-plus word tome, dropped on Ars Technica, a technology site owned by Condé Nast, to ritual fanfare and millions of hits. Then he returns to his job as a Web developer in Massachusetts.

The focus of Siracusa’s criticism is, of all things, Apple’s operating system.

His loyal following comes in part from drilling comprehensively—perhaps more thoroughly than a staff critic with multiple deadlines could handle—into a niche product. Another is the deep technical knowledge he brings, coupled with decades following the business and culture of Apple (he had a picture in his childhood room of the original Macintosh team). “He’s iconic. The canonical nerd,” said Philip Elmer-DeWitt, whose own technology coverage dates back over three decades, and today writes about Apple for Fortune.

Perhaps unsurprising given Siracusa’s techie fan base, his pieces have translated well to new media too: since 2011, in addition to their release as articles on Ars Technica, the reviews have sold as $4.99 ebooks on Amazon and iBooks, garnering thousands of sales.

Still, why does criticism about Apple’s operating system matter? For one, it reflects the story of Apple the company, whose game-changing contribution to computing was humanizing it with the now-ubiquitous desktop, folders, and mouse. Ever since, Apple has been the company of aesthetics and usability within the cold, efficient tech world. But the operating system is also the medium through which we have every interaction with our phones, computers, and tablets. The development of the operating system tracks the story of the human relationship to technology.

As Siracusa works on his latest review for release this fall, CJR caught up with him about the evolution of the Apple narrative, the company’s tense relationship with the press, and what longform software criticism can tell us about the enigmatic technology giant.

How has Apple coverage changed over the years? 

You had this comfortable equilibrium [in the 1990s] where the Apple fans were the underdogs—the rest of the world more or less ignored them because everybody used Windows and there was the near-death moment where Apple almost went away. We know what happened next: The iMac and the iPod led to Apple’s resurgence, then of course the iPhone and the iPad. Fast-forward to today, and Apple is no longer the underdog. You can’t cover Apple or write about Apple as if it’s the scrappy upstart competitor fighting against the Windows monopoly.

That is what I think is the modern ailment of coverage of Apple: people who remember it back from the day when it was a small underdog and have not adjusted the way they view it to account for the reality of today’s Apple. They are now big enough and powerful enough that you have to watch for their use of that power and that money much more closely.

To the credit of the non-enthusiast media, they never had a problem with that because they were never so emotionally invested in Apple. So when The New York Times did the story about labor practices in Apple’s factories, [Apple enthusiast outlets argued that] Apple is no different from tons of other companies that manufacture products overseas in this respect. But if you had to pick one story, if you didn’t pick the biggest technology company in the world wouldn’t that be weird?

And I don’t think Apple helps with the secrecy. The press wants access, and Apple doesn’t give access. And so there is a resentful relationship between the press and Apple.

Has that relationship between Apple and the press changed at all over time?

The old slogan about Apple was it was a strange ship: the kind that leaks from the top. Back when Apple was tiny and going out of business, their executives were talking to the press all day—off the record, on the record, they were leaking all over the place. Pretty much as soon as Steve Jobs came back, he put a stop to that. It was total radio silence. And they weren’t in a powerful enough position to do that at that point, because they were still on the verge of going out business.

It was like dressing for the job you want to have. Or they said, “This is the kind of company we want to be now.” They honed that strategy over the years, and now it’s just the way they operate.

Is the grander narrative of your articles about where Apple is headed?

It’s like criticizing your children. Because I like Apple so much I want to make sure they’re not doing anything that will be a problem later. And this comes from the experience of Apple nearly going out of business in the ’90s. They’re no longer that underdog, but I’m looking at everything they do and saying, “Are you doing everything you should in the way that you should? Are your products living up to the ideals you set for yourselves?” I don’t write these reviews of Windows. I could never muster up the enthusiasm or indignity.

In your 2009 article, “Hypercritical,” you make a comparison between tech criticism and movie criticism. How can you inject emotions, which you normally associate with criticism of the arts, into technology?

I think around the time of the dawning of the internet was the same time that computer hardware and software started to be recognized as more than the sum of its specifications. Just look at the iMac, which was a fine computer spec-wise but was teal and translucent. Why does that matter? Does it matter what a button looks like? Does it matter what the color theme of the thing is? Do animations make the operating system better? No, in fact it slows it down. But there is a user experience that is far beyond just what the specs are.

What I find interesting is the huge market for reading these pieces despite their length. In the media industry, it’s hard to get pieces published that are more than a few thousands words. Was that surprising to you?

Well it wasn’t a surprise, because I knew that there were people like me out there who wanted to read this type of thing. And the more rare something is, the more enthusiastic people will be about it. If you’re super into technical details about an operating system, no one was writing about this [when I started]. And that drives loyalty. That drives people associating your name with that experience. And it’s only once a year.

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Chris Ip is a CJR Delacorte Fellow. Follow him on Twitter at @chrisiptw.