The window shades are halfway down, leaving the bedroom dim. It's a grim day in Bassano del Grappa, a town in northeastern Italy that's mostly famous for its main import, the liquor of the same name: Grappa. I'm sitting on a twin bed—the only place I could sit. To my left, there's a bookshelf with a stack of Mickey Mouse comics, a staple in the childhood bedroom of every Italian kid. In front of me, sitting in a faux racing car chair, there's Luca Todesco, a 19-year-old who might be the best iPhone hacker on the planet.
"These are features that you have on a phone, and these are features that the iPhone did not have," he said. "The iPhone came out and it was essentially a small tablet web browser that happened to sort of have a crappy phone wedged on it."Those were the Wild West days of jailbreaking, when talented, albeit amateur, hackers did it for fun, and to screw with Apple's walled garden.
"The iPhone came out and it was essentially a small tablet web browser that happened to sort of have a crappy phone wedged on it."
That was a turning point. Wang, who goes by the handle planetbeing, posted his instructions online a few weeks after geohot's famous video, and it set off a frenzy. "So if you Google '74-step jailbreak,' you would see my name," Wang says. "It was the first thing that I did."That's how jailbreaking became the popular term for knocking down the iPhone's security system, and allowing users to treat the device as an actual computer—modifying settings, installing new apps, etc.Shortly after, Wang saw a blog post by the security expert HD Moore, who'd taken apart, step-by-step, that TIFF exploit. Moore had, in essence, laid out a blueprint for an automatic jailbreak.Wang wrote the predecessor to what would later become perhaps the most legendary—and trivial to implement—iPhone jailbreak mechanism. Instead of 74 steps, this jailbreak only required visiting an online "app" through Safari, a website called JailbreakMe.com, that would immediately jailbreak the phone.The first JailbreakMe, also known at the time as "AppSnapp," was released in October 2007, and soon became the stuff of legend.
"Every product starts out in an unknown state."
Unlike those unknown malicious hackers, the vast majority of the jailbreakers, like Wang, did it for the sport of it, and because they were eager to expand the capabilities of a clearly capable machine. The majority weren't hacking into anyone's phones (besides Apple Store display models, an easily reversible prank) and were only jailbreaking their own to customize them.
"People will try to break in, and it's our job to stop them breaking in."
In January of this year, Todesco announced that his jailbreaking career was done."PSA: I will stop all public iOS research after I drop that 10.2 thing. The idiocy of the jailbreak community is too much to handle for me," he tweeted, before clarifying that "by 'public research' I mostly meant 'public [jailbreaks].'"When we met with him in December of last year, Todesco complained about the toxic environment in the modern jailbreaking community, where people bombard hackers like him asking for jailbreaks. These nagging requests for a timeline—"wen eta jailbreak?"—on the next jailbreak have become sort of a meme.Things indeed have changed."I feel like jailbreak's basically dead at this point," Allegra said in a recent chat through iMessage.Allegra said that if there was anybody who was going to "revitalize" jailbreaking, it would have to be Todesco. When we told him the Italian hacker had announced he was giving up jailbreaking, he wrote: "Oh? Too bad."For Freeman, the father of Cydia, a man who's seen countless jailbreaks, it's basically all over. Back in the good old days, he says, jailbreaks would work for months. Now, when there are public jailbreaks, they get killed immediately."Apple has both upped priority on fixing jailbreaks but also we have moved so far up the stack that we're actually dangerous," he says.Once a jailbreak crusader, it's gotten to the point where Freeman no longer recommends that people jailbreak their phones. It's dangerous, due to the higher risk of getting hacked, and it's not even worth it anymore, he says in a recent phone call."What do you get in the end?" he asks. "It used to be that you got killer features that almost were the reason you owned the phone. And now you get a small minor modification.""That turns into, like, a death spiral, where when you get fewer people bothering to jailbreak you get fewer developers targeting interesting things, which means there's less reasons for people to jailbreak," he added. "Which means there's fewer people jailbreaking, which causes there to be less developers bothering to target it. And then you slowly die."This story was adapted from an excerpt of The One Device: The Secret History of the iPhone , with additional original reporting.Motherboard staff is exploring the cultural, political, and social influence of the iPhone for the 10th anniversary of its release. Follow along.Get six of our favorite Motherboard stories every day by signing up for our newsletter.
"I feel like jailbreak's basically dead at this point."