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The race to jailbreak the iPhone 5

The iPhone 5 has gone on sale this morning, which means that some of the world’s most tenacious hackers have now begun to tackle the tricky task of jailbreaking Apple’s new smartphone. To date, every single iPhone has been cracked wide open by hackers, blazing the trail for tethered and eventually untethered jailbreaks. Every year, Apple releases new products with increasingly complex security measures – and yet, without fail, they fall to the increasingly tenacious attacks of Apple hackers.

How does a hacker jailbreak an iPhone or iPad, though? Well, I’m glad you asked, because the answer to that question is rather interesting.

Defining the problem

To begin with, hackers aren’t interested in hacking the iPhone 5 itself – they’re actually looking for a flaw in iOS 6 and the A6 SoC, both of which are brand new and relatively unknown. In the case of the iPhone 4S, it withstood hacking attempts for months – much longer than any other Apple device – before it finally fell.

To create an untethered jailbreak for the iPhone 5, hackers will first have to find an exploit in the iOS 6 kernel, and then they’ll have to work out a way of circumventing the hardware-level security provided by the SoC so that they can inject arbitrary, unsigned code into the boot ROM – the first code that is executed when an iDevice is powered on. This custom code will disable the iDevice’s security features, allowing you to install non-App Store programs, such as Cydia. Voila, one jailbroken iPhone.

Finding a kernel exploit

On something like a Linux PC, where you have full access to the source code and the ports on the back of the computer, finding a kernel exploit is relatively easy – it’s just a case of painstaking analysis, leaving no stone unturned. iOS source code is closed, however (though XNU, which it is based on, is open source), and the hardware is relatively locked down.

In the case of iOS 4 and 5, both of which have been jailbroken, the kernel has a built-in debugger – a tool that spits out a lot of information about the kernel’s behaviour, so that Apple’s internal software team can find and squash bugs. This debugger is only accessible via serial connection, however – and obviously, the iPhone doesn’t have a serial connector on the bottom. Or does it?

It turns out that the old 30-pin Apple connector actually has two pins set aside for serial communications – and to use them, all you have to do is solder together a few simple components that can be bought for around £20 or so.

With the homebrew cable made, an Apple hacker can open a serial connection with the iDevice, gaining access to the kernel debugger. Once you have access to the kernel debugger, it’s a matter of finding an exploit – a flaw in the kernel that can be used to gain root access to the device. This step is incredibly complicated, requiring a vast amount of software expertise. For more info, check out Stefan Esser’s excellent Black Hat and CanSecWest [PDF] presentations on iOS kernel exploitation.

Tethered or untethered?

Once you’ve found a kernel exploit and gained root access, you have achieved a tethered jailbreak. If the hacker can also find a vulnerability in the device’s hardware-level security (as Limera1n did with A4-based iDevices), then the exploit can be loaded into the boot ROM and executed every time the device is powered on – an untethered jailbreak.

In the case of Apple’s A5 SoC, which debuted in the iPad 2 back in the spring of 2011, it took ten months to find an exploit that would allow an untethered jailbreak. In the words of a Chronic Dev Team spokesperson: “I don’t know if any iOS hacker anticipated how much the A5 chip would completely change the game and up the stakes. The endless war we fight to jailbreak has become more and more difficult with each new device released, and our recent battle against A5 only proved this further.”

Jailbreaking the iPhone 5 and A6 SoC

There’s the matter of the new Lightning connector, too. I suspect it doesn’t have dedicated serial pins, which will add another layer of complexity that will need to be reverse engineered by the iDevice hackers. There is one possible glimmer of hope in that iOS 6 has already been jailbroken – but only on antiquated A4-based devices (iPhone 3GS/4), and it’s still only a tethered jailbreak.

Will the A6 fall? Will the iPhone 5 be jailbroken? If history has taught us anything it’s that nothing is truly secure. Given enough man hours, an exploit will be found.

Apple doesn’t need to make the iPhone 5 completely secure, though – it just needs to last a couple of generations, until the next upgrade cycle. Given Apple’s continued investment in security and the news that the A6 SoC features a highly customised in-house design, I wouldn’t be surprised if the iPhone 5 isn’t jailbroken for a long time to come.

Want to read up more on Apple's new smartphone? Then try browsing some of our head-to-head spec comparisons, with the iPhone 5 pitted against the Nokia Lumia 920 here, the Samsung Galaxy S III, the HTC One X, and the Galaxy Note 2.