Design Con 2015

The jailbreak: When playing cat-and-mouse with Apple, it pays not to wait

-February 28, 2013

As I type these words, I'm frantically downloading iOS v6.1.2 to my "iPad 3," which is currently running iOS 6.1.0 (6.1.2 fixes an Exchange bug). I've already updated my two iPhone 4s, which were previously on iOS 5.1.1, to iOS 6.1.2. And next on the upgrade list is my fourth-generation iPod touch, also currently running iOS 5.1.1. So what's the rush ... what's with all this "frantically" business?

I'm admittedly doing a belated upgrade of my iOS 5.x-based widgets, considering that iOS 6.0 was released last September. I'm already running into a few situations where I can't update to newer versions of some of the programs already installed on my devices, or for that matter install some new software titles, in both cases because the new code requires iOS 6.x. Whether the software truly taps into some iOS 6-only resources or the developer just left the Xcode compiler switches at their defaults, therefore conveniently enabling Apple to compel consumers to tackle periodic O/S upgrades, is unknown ... regardless, the end effect is the same, overriding my "if it's not broken, don't fix it" tendency to leave well enough alone.

But why am I rushing to do the upgrades now, versus further procrastinating? It's because all of my iOS devices are jailbroken, thereby enabling them to support additional (non-Apple- and non-carrier-sanctioned) capabilities such as gratis cellular-modem tethering to my laptop, full file system access via SSH, etc. It's because the latest-generation jailbreak tool, Evasi0n, supports iOS 6 versions through 6.1.2. And it's because iOS 6.1.3, currently in beta, reportedly breaks Evasi0n.

Again, you might ask, what's the big deal? I don't need to upgrade all the way to the latest and greatest iOS release, do I? Actually, I do. As soon as Apple releases an O/S up-rev, it removes "signing" authority for the previous O/S version. Although plenty of iOS version archives exist (Felix Bruns' is probably the best known) they're of no practical value if Apple's servers don't allow use of the firmware images found there. A utility called TinyUmbrella supposedly "spoofs" iTunes into thinking it's talking to an Apple server, thereby creating a "signing" loophole, but I've never been able to get it to work.

So upgrade I go. It's a hassle, thereby at least partially explaining the above-mentioned procrastination. I can't update the O/S without wiping out the jailbreak (and the additional utilities I've installed subsequent to it) in the process. And I can't even do a "normal" over-the-air or iTunes-tethered upgrade, because the jailbroken state of the hardware will result in a failed update attempt. Instead, I need to put each device in DFU mode and install the O/S upgrade that way, a procedure that wipes the device completely clean in the process. Thank goodness iOS now supports iCloud account-based backups and restores, which make subsequent resurrection much easier than it used to be. Then I need to re-jailbreak each device. And then I need to reinstall each device's Cydia-sourced jailbreak software suite.

Is it all worth it? That's a question I ask myself each time I go through one of these cycles. The answer: probably not as much as it used to be, particularly now that Apple officially supports capabilities such as multitasking that used to only be (clumsily) capable via a jailbreak. But still, the answer is "yes." Some of the reasoning is for the "big things"... the aforementioned fee-free tethering capability, particularly attractive given the unlimited-data plans on each of my devices. And some of it is for the "little things" that I still miss when they're absent, such as the ability to precisely place the cursor via a slick utility called SwipeSelection.

So upgrade I go ...

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