Confessions of an iPad Jailbreaker (or Why and How I Jailbroke my iPad)

About a month ago, I decided to pony up the money and buy myself one of those new fangled iPads. I’m not going to go into the reasons why I bought one (after all, this is an article about what I did after I bought one, not the reasons why I bought one). The first thing I did after I unwrapped it and did the initial sync with my machine was to jailbreak it. Jailbreak? What exactly is this “jailbreak” you speak of? Well, as Amy discussed earlier today, jailbreaking is a term that refers to any process by which you unlock a device’s operating system, providing root level access in order to run unassigned code (“unassigned” basically refers to code that doesn’t have the secret key required to run it on the device in question—which pretty much boils down to a device’s official and approved software). The term “jailbreak” is most commonly used in reference to Apple devices (specifically iPhones, iPods, and iPads). As Amy has already noted, the term “root” is used in the Android world. You’ll also see the term “mod” or “hacked” used in reference to game consoles (such as the Xbox 360) or handheld game devices (such as the PSP or DS). Ultimately, all of the terms refer to the same above-mentioned process.

The Why

Ok, first the big question. Why did I jailbreak my iPad (we’ll get to the how a little later)? For me, it came down to several things:

Multitasking
Easily the biggest reason that I decided to jailbreak my iPad was in order to enable multitasking. iOS is historically notorious for being a unitasking device. The problem is that the iPad is more computer-like (compared to the iPhone or the iPod). The result is that you will often find yourself in a situation where you wished that you could run a couple of apps concurrently, switching back and forth between them. The “stock” (i.e. un-jailbroken) iPad just doesn’t allow you to do this. However, once you’ve jailbroken your iPad, you can install a handy little app called Backgrounder. After it’s installed, Backgrounder lets you force apps into the background with a press and hold of the home button (you can actually configure the trigger if you want via Activator, a handy utility that comes along with Backgrounder). The end result is that I can listen to Pandora while reading digital comics.

File Management
Besides the lack of multitasking, one of my biggest complaints about the stock iPad is that it’s a bit of a black box in terms of files. It doesn’t come with a file management application that lets you navigate its directory structure and files. This is easily remedied when you jailbreak your iPad. I use two apps in particular. The first, OpenSSH, enables connections to the iPad over Wi-Fi. It gives you full access to your iPad’s file system from your computer. The best thing is that once OpenSSH is installed and configured (you’ll need to connect to your iPad from your computer using an SSH program), it’s just there—no app to run, no settings to mess around with. The second of the apps that I use for file management is iFile. While OpenSSH lets me transfer and manage files wirelessly from my computer, iFile gives me the ability to navigate my iPad’s files from the device itself. iFile lets you do all of the typical file management stuff—moving, renaming, deleting, folder creation, etc.

Style/Themes/UI
I’m a UI customization junky. I really like to mould a device’s UI like warm putty. I like icon sets, themes, styles, custom docks—you get the idea. The problem with the iPad is that it is really short on ways for me to indulge my UI customization inclinations. Yes, you can change the screen’s background and move the app icons around, but that is about it. With a jailbroken iPad, your UI customization options are a little broader. The Winterboard app gives you access to a wide variety of themes and docks, while the Categories app lets you organize icons into folders. A couple of caveats for both of these apps: first, most of Winterboard’s themes are designed for the iPhone, and not the iPad. As a result, most of them look pretty bad when used on an iPad. Second, Categories works just fine—it does exactly what it is supposed to do (and does it well). However, it doesn’t have the UI elegance of folders in iOS 4 (granted, the issue of iOS4 on iPad is moot at this stage of the game).

Device Control
“Device Control” pretty much covers everything else under the sun that doesn’t fit into one of the previous categories. To be fair, the iPad covers this fairly well. There are, however, some things that could use some tweaking or enhancement (things that can only be accomplished when you go down the jailbreaking rabbit hole). So, for instance, SBSettings adds an always-available (and completely configurable) control panel for important settings (such as brightness, wifi, processes, rotation, etc.).

Putting My Money Where My Mouth Is
While the least tangible, this final motivation is probably the most powerful reason (personally) why I jailbroke my iPad. There is a lot of concern (both in and out of the educational community) about the closed nature of the Apple ecosystem (both hardware and software). As I am an adherent of open access (especially in the context of the academy), I agree with most (if not all) of these concerns. However, I’ll be the first to admit that the iPad is a right sexy wee device that does a lot of things really well and has a lot of potential uses in the academy. So, how do I reconcile these two thoughts? Well, I jailbreak my iPad, thats how! By jailbreaking, I’m (in a sense) liberating my iPad from the oppressive shackles of Apple’s closed ecosystem while still being able to take advantage of what is a pretty good device with a lot of exciting potential.

The How

Jailbreaking an iPad is dead simple. I’ve got to be honest, compared to all of the other jailbreaking/rooting/modding/hacking I’ve done on my other devices (I’ve hacked/rooted/jailbroken my Xbox, my PSP, my Droid, my DS, and my iPod), the process of jailbreaking my iPad was so incredibly simple that I was left feeling like I hadn’t earned it somehow. But no matter.

All you need to jailbreak your iPad is a computer, an activated iPad, iTunes (any version earlier than 9.2), and a little program called Spirit. Spirit is a jailbreaking application that works on Mac, Windows, and Linux. A couple of really important caveats if you are planning on using Spirit to jailbreak your iPad:

• Spirit is not a carrier unlock. By this, I mean that if you have a 3G iPad, you can’t use Spirit to tap into another 3G network.
• While Spirit is pretty stable, any rooting/jailbreaking/modding/hacking brings the danger of bricking your device. Bricking basically means that something might happen during the process that irreparably damages your device, so much so that it cannot function at all—turning it into a “brick.”
• As Amy has already mentioned, jailbreaking voids your iPad’s warranty & violates your terms of service. Granted, if you do find that you need to return or exchange your iPad, you can restore it to factory default—thereby wiping out any trace of the jailbreaking.

So, you’ve been duly warned. On to the simple how-to!

1. Download and launch the Spirit application
2. When prompted, plug in your iPad (just in case, make sure it has been backed up first)
3. Hit the “Jailbreak” button (the Spirit app only has the one button, so its hard to miss—seriously)
4. Wait for the spinny, “I’m busy doing something” wheel to finish spinning and the “Jailbreak Complete!” message to appear
5. Hit the Quit button, and your iPad will reboot.

Voila! Your iPad is now jailbroken. The only difference that you’ll notice is that you’ve got a new app called Cydia sitting on your home screen. Cydia is the other part of the jailbreaking equation (and is automatically installed when you use Spirit). Think of Cydia as your app store for the jailbroken iPad. It essentially acts to aggregate application repositories from trusted developers. Most (if not all) applications that you are going to want to install on your newly jailbroken iPad are available via Cydia. While the majority of apps on Cydia are free (or freeware), there are some paid apps (one of the most noteworthy is Mifi, which gives you the ability to turn your 3G iPad into a wifi hotspot). Most developers accept payment via Amazon Payments or PayPal. As a quick aside, just because your iPad is jailbroken doesn’t mean you can’t buy apps from the iTunes store (just like you would with an un-jailbroken iPad). Th slight caveat in this is that I’ve personally run into two “official” iPad apps that I purchased through the iTunes store that did not work on my jailbroken iPad: Air Sharing HD and BeeJiveIM.

Final Thought

Jailbreaking isn’t something that sticks when you upgrade your OS. So, when Apple finally releases iOS4 for the iPad your iPad will “un-jailbreak,” and all of the apps you installed via Cydia will cease to work. But let’s be completely honest here. Even though Apple is trying extra hard to make jailbreaking impossible on future version of iOS, I’m pretty sure that a method of jailbreaking an iOS4 iPad will come almost immediately after Apple actually releases iOS4 for the iPad.

Did you jailbreak your iPad? If so, why (and what are you running on it)?

[Creative Commons licensed photo by Flickr user genista]