Jailbreaking the iPad is stupidly easy. But even so, why bother? What's in it for you and your tablet? Here are 16 of the best, most useful apps and tools for jailbroken iPads. UPDATED: New guide here.
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Backgrounder: By far the most important jailbreak app for the iPad, Backgrounder addresses the iPad's biggest software shortcoming, at least until OS 4 comes out of beta: its lack of multitasking. Once Backgrounder is installed, all that's needed to force an app like Pandora into the background is a press'n'hold of the home button. You can add other triggers too, via Activator. (My personal favorite is "Status Bar Hold.")
Activator: A gesture framework that's automatically installed with Backgrounder, though there's a downloadable front-end for the app that's worth nabbing. Anyway, this lets you assign a huge variety of triggers and gestures to system functions. For example, when I shake my iPad, it takes a screenshot. Ha!
Veency: A VNC server for your iPad. This lets you open and control your iPad from any computer on the same network (or conceivably from outside the network, if you've forwarded the right ports to your iPad). The zero-setup app comes with a mouse framework, so you'll see a cursor on the iPad as it's being remotely controlled. Super cool as a tech demo, and surprisingly useful—it's a nice way to add your iPad to your main computer setup.
SBSettings: This app adds two important features to the iPad: advanced settings, and an always-available control panel for the more important ones. Many gestures are available (via Activator); I've got mine set up so that when I pinch my homescreen, the control panel slides down.
The panel can be populated with just about any setting you could imagine, but Wi-Fi, Bluetooth and Brightness toggles are must-includes.
FullForce: A clever little extension that installs to the iPad's settings screen. From there, you can designate iPhone apps—the ones that haven't been properly adapted for the iPad yet—to stretch out to the iPad's resolution. I'm not talking about pixel doubling, either: apps employ native UI elements, and scale dynamically.
The success rate isn't spectacular, and it rarely works with games. That said, apps like Facebook and NYTimes (which has much more content than the iPad NYT app) scale perfectly, and fill a need. FullForce works on most jailbreak apps, too, including a few in this guide.
WinterBoard: Themes! Well, sort of. Most of the Winterboard-compatible themes available in Cydia aren't designed for the iPad, so they look terrible. But hey, you can fiddle around with the dock, with some fonts, with some coloration, and so on. More iPad themes will come in due time.
MyWi: Tethering for the 3G iPad, weeeeee! It's a paid app, but you can trial test it for free. It creates a local Wi-Fi network which you can connect to with anything, from a laptop to a Wi-Fi-only iPad.
MultiIconMover: Moving icons one by one is a pain in the ass. MultiIconMover adds a clever little behavior to the OS, such that when icons are in wobbly (moving) mode, they can be flagged for movement with a single tap. Once the apps are selected, the user simply switches over the the screen he wants the apps to move to, taps the home button, and the deed is done.
Cydelete: If you've read this far, you've probably got a stack of new icons on your homescreen, courtesy of Cydia. One problem: You can't delete them like normal apps. (Instead of the simple X-delete convention, Cydia apps depend on management from within Cydia. Lame!) This brings back the little "X", so you can nuke the Cydia apps you don't want to keep, conveniently.
OpenSSH: Allows connections to the iPad over Wi-Fi, and gives you full access to the device's file system from your computer. Once it's installed, it's just there—no app to run, no settings to mess with.
This is the easiest way to move files to the iPad for jailbreak apps, like VLC and game emulators, to access. Instructions here.
vlc4iPhone: This one's rough around the edges, to be sure. It works with FullForce, sort of, and it crashes fairly frequently. But just consider the potential here. VLC plays just about any video file, whether or not it's supported by iPhone OS. Movies could be dragged over to the iPad via SSH and played without the need for conversion. This is the vision that vlc4iPhone more or less fulfills, and which it will soon fulfill on the iPad.
Installous: I wasn't sure about including this one, but it's a popular component of the jailbreak experience, a driving force behind its popularity, and, what the hell, you'd find out about it anyway. (Name that logical fallacy!)
It's necessary to add special a repository to Cydia in order to get this one, but once you've done that, the rest is cake. If you must use it, please treat it as a try-before-you-buy tool. Devs gotta eat.
Wi-Fi Sync: $10 for a jailbreak app? Before you laugh, hear this: Wi-Fi sync syncs your iPad with iTunes over Wi-Fi.
Rock: An alternative to Cydia, Rock offers a different interface, and more importantly, a useful framework for app trials. (More and more jailbreak apps are going paid, so this matters.) I prefer the interface to Cydia's, but find it less stable. UPDATE: Cydia has merged with Rock, and is in the process of combining stores. Cydia IDs won out in the end, so Rock users will have to switch to those.
Categories: This one's simple enough: Folders for your apps, like the ones in OS 4, except uglier and available right now.
iFile: A file manager for the iPad. This becomes more important when you're SSHing files back and forth for emulators and the like, as it gives you a browsable file tree.
This list is by no means exhaustive, so tell us about your favorite jailbreak apps in the comments.