If you're convinced that the walls surrounding the iPhone OS garden are a little too high, jailbreaking is your ticket to freedom. Here's how to bust your iPad out, and why you might want to do so.
How easy is it to jailbreak my iPad?
Stupid easy. The Spirit jailbreak is literally a one click process. Just sync your iPad to make sure everything on your computer is up-to-date, download the Spirit jailbreak application for Mac or Windows, and follow the instructions. In fact, what's most important during the install process is what you shouldn't do, which is to say, pretty much anything. Don't try to fool around with your iPad or iTunes and definitely don't unplug the device while the jailbreak is taking place. Just let Spirit do its thing and you should be fine.
What can a jailbroken iPad do?
First and foremost, multitasking! Backgrounder, an iPhone jailbreak favorite, works beautifully the iPad, allowing you to finally realize that elusive dream of browsing the web to a Pandora-provided soundtrack.
The vast majority of things, on the other hand, don't work as beautifully. Task switchers like ProSwitcher and Kirikae are a no-go so far, though their developers are working on updates that'll work with the iPad.
Basically, the consensus is that it's best to only install apps that have been specifically updated for the iPad. The rest, at best, will half-work and at worst could cause some serious problems. It's likely that Cydia—which itself has a new and improved, iPad-friendly interface—will eventually be full of apps that work swimmingly on the iPad, including pretty much all of the things you know and love on your jailbroken iPhone.
In the meantime, MacStories has a continually updating post of which popular jailbreak apps work on the iPad and which don't, and there's a similar thread on iPadForums in which courageous iPad jailbreak trailblazers are reporting their various successes and failures. Both of these are definitely worth consulting if you take the leap.
What is Cydia?
Cydia is jailbreak HQ, the unofficial app store that gives you access to all of the goodies Apple doesn't allow. After you jailbreak, Cydia will show up as an app like any other, and from there you can download and install Backgrounder and the rest.
Is this going to destroy my iPad?
Probably not. If you stick to Cydia apps that have been updated for use with the iPad, you should be fine. But things are definitely still rough around the edges, and if you just start installing stuff from Cydia willy-nilly, you could seriously mess things up. Stray too far form the beaten path and you might find yourself in a situation in which a factory restore is required, and though there haven't been any reports of it so far, there's always the outside chance that you might brick your iPad altogether.
It's also important to keep in mind that no one is sure how this will work with future upgrades, and once Apple starts trying to patch the holes that make this jailbreak possible, things could get very sticky. So, as always with these sorts of things, proceed with caution, and saving your SHSH blobs is always a good idea.
Things are definitely still rough around the edges, so while the process is easy enough, jailbreaking's still not for the squeamish.
Does this void my iPad's warranty?
Yes. When you jailbreak, you're going off the grid. Apple Store Geniuses, usually a chipper, enthusiastic bunch, will regard your jailbroken device with icy indifference. Of course, restoring your iPad to the original, factory settings should get things back to normal, without anyone ever knowing of your shameful jailbreak secret.
If I jailbreak can I download App Store apps for free?
Yes. Not that we condone this—and I'm not being coy, we really don't—but jailbreaking will let you circumvent the App Store and install many popular apps and games for free. We're not going to get into the specifics here, but if you search around you should be able to get the gist of it.
Will jailbreaking affect my App Store apps?
Nope. You can still use your old apps from the App Store, buy new ones, and sync them to your computer just like normal.
What does it mean that this is an "untethered" jailbreak?
Basically that you don't have to have your iPad plugged in to your computer—or "tethered"—every time you start it up. That's a good thing!
Oh no my iPad looks all crazy and the dock is tiny in the bottom-left corner! What do I do?
This is a known bug with some Cydia apps, like SBSettings. Just "respring"—either in the SBSettings menu or by restarting your iPad—and things should pop back to normal.
OK, that was exciting, but how do I get my old iPad back?
Restoring your iPad to factory settings in iTunes will remove all traces of jailbreaking activity and let you resume your tranquil existence inside Apple's walled garden. Oh well, it was fun while it lasted.
And remember, be careful! Jailbreaking is unsupported and something that's very new to the iPad. If in doubt about a particular Cydia app, err on the side of caution. You're better safe than sorry, really.