Jailbreaking Gets Back In The Game With iOS 7

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In the final months leading up to the next major iOS release, there’s barely enough activity on the jailbreak front to fill a couple of conference rooms. But with the public release of iOS 7 just around the corner, it’s like the calm before the storm as hackers gear up for what may be the toughest system to crack yet.

Developers, hackers, and hardcore fans gathered in late August at JailbreakCon in New York City, an annual summit for the meeting of the minds within the jailbreak community. And while the conference’s founder, Craig Fox, wasn’t “overly pleased” with attendance for the third edition, he still considers the event a success. Why? It fulfilled its mission.

For the past few years, JailbreakCon has played a crucial role in providing face time to code jockeys from different continents who would otherwise only know each other by Twitter handles. Friendships are formed and ideas are shared. This year was no different. And as the release of iOS 7 draws near, jailbreaking’s closely-knit group of hackers and developers is getting back in the game.

Jailbreaking is the art and science of removing the restrictions Apple places on its devices. Jailbreaking provides root access to a device’s operating system, allowing users to install unsanctioned apps, extensions or themes. It’s the anti-Steve Jobs approach. The device is broken out of jail. Jailbreaking was never easy but now it’s getting really hard.

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“The goal is to keep jailbreaking sustainable”

Slow and steady appears to be the future of jailbreaking: the least flashy and yet most important development is OpenJailbreak.org, a project spearheaded by veteran jailbreak hacker Joshua Hill.  The talent pool for jailbreaking, while incredibly proficient, is much smaller than the throngs of developers making apps for the App Store. For instance, the hackers responsible for releasing the last evasi0n jailbreak for iOS 6 can be counted on one hand. The level of technical expertise required to create a jailbreak would raise eyebrows at the NSA, so finding fresh talent is particularly difficult.

“Apple’s hardware has gotten more difficult to hack over the years”

OpenJailbreak plans to help by crowdsourcing security research for future jailbreaks. It’s meant to serve as a safe forum for collaboration. “The goal is to keep jailbreaking sustainable” as security exploits become harder to find, Hill explained at JailbreakCon. Apple’s hardware has gotten more difficult to hack over the years. For instance, the third-gen Apple TV has still not been jailbroken. According to the set-top box’s main hacker, Kevin Bradley, it probably never will be cracked.

How can a device be uncrackable? The process of creating a jailbreak is like assembling a puzzle in the pitch dark. First, jailbreak developers have to find vulnerabilities, or security exploits, in Apple’s code and string them together together to get into the basement of the filesystem, otherwise known as root access. While finding these exploits obviously requires a lot of reverse engineering talent, much is still left up to chance. Once root access is gained, they can make the operating system do just about anything they want without Apple’s permission. But sometimes jailbreak creators can’t find ways to string exploits together, as is the case with the third-gen Apple TV. Sometimes puzzle pieces stay missing.

With the rare exception of a device like the most recent Apple TV, the jailbreak cycle happens like clockwork every year; Apple releases a new iPhone or iPad alongside a major iOS software release and a new jailbreak comes out months (sometimes weeks) later. Millions (yes, millions) of people then jailbreak, and Apple releases updates to patch the security vulnerabilities that were used to create the jailbreak in the first place.

As the months wear on, jailbreaking becomes less relevant and eventually iOS is updated so many times that only diehard jailbreakers remain faithful.

This core crew is gathering steam for TweakWeek, a hackathon of sorts organized Ryan Petrich, perhaps the most prolific tweak creator in jailbreaking history. A dream team of top developers has been assembled to release an open source tweak in Cydia (the unofficial app store) each day for one week for the second edition. Developers like Adam Bell, who brought Facebook Chat Heads to iOS before Facebook did, are contributing. The event won’t kickoff until the iOS 7 jailbreak is released, and based on history, that’s week’s away.

Bigarella plans to continue developing and doing freelance work while attending college this fall.
Bigarella plans to continue developing and doing freelance work while attending college this fall.

One developer participating in TweakWeek 2 is Filippo Bigarella, who is best known in the community for creating Springtomize. Bigarella, who just graduated from high school in Italy, personally sponsored JailbreakCon with the money he has made as a developer as a way of giving back.

Bigarella is in an interesting position because he makes apps for Cydia and the App Store. “Even though you’re targeting the same devices, developing for the App Store and for Cydia presents many differences both in the development process and in the final audience of your products.” Not only does Bigarella know how to make regular iOS apps, but he has a more fundamental understanding of how the operating system works on a technical level, which gives him an advantage as a developer.

“Jailbreaking is by no means dead”

While the future of jailbreaking isn’t totally certain post-iOS 7, Bigarella has high hopes. Hackers who worked on the iOS 6 jailbreak have exploits saved for iOS 7, which could theoretically speed up the process cracking the code for public use. But as always, jailbreaking remains at the mercy of Apple. While the security exploits related to jailbreaks are usually patched pretty quickly with updates to iOS, Apple has historically ignored the jailbreak community.

“If there is anything I can stress, it is that jailbreaking is by no means dead,” said Conrad Kramer, another young developer who attended JailbreakCon. The “far from dead mantra” is what jailbreakers almost universally agree upon. Craig Fox is currently gearing up for next year’s JailbreakCon in San Francisco, where he expects attendance to be the highest it has ever been.