I've got a good bit of experience with the jailbreaking scene and thought i'd clear a few things up for those who may be new to this. I'm going to cover the only two things you really need to know: what advantages are there to jailbreaking your iPad, and are there any reasons not to. Once you've jailbroken your device the only visible difference at first will be 1 extra icon on your springboard called Cydia. You can think of this as the 'AppStore' for things that Apple has decided not to allow (read: all the stuff you really want). All of the programs I will mention below are available there. As in the AppStore, most of the items are free to download, some aren't. These apps are the reason you jailbreak, and I'll go over some of my favorites now. For starters there's winterboard. A full theming utility which will allow you to install any of the hundreds of themes that are out there. Change the look of your icons, remove icon labels and so much more. Backgrounder allows for full backgrounding of applications so switching back and forth is instant and your streaming music won't stop when you want to do something else. You could wait the months it takes for 4.0 to come to the iPad, but you don't have to... How about iFile? A file explorer just like you're used to on the computer. Pair this with ssh and now you have an easy way to transfer files to the iPad without iTunes. One example use is that you can transfer an mp3 to your device and use one of the free music players in Cydia to play your iPod music and your transferred mp3's. You could also just use this method to take a large file over to a friends house rather than using a USB stick. More awesome tweaks than you can shake a stick at like this one. Hate the typical process for moving lots of icons around across multiple screens? You need to try MulitIconMover! Wow! Can't believe I'm only getting to this one now. Probably my most essential is Safari Download Plugin. Tired of seeing 'Safari cannot download that file'? Yea I was too, but now I browse to an mp3 on the web, download it right to my device, then play it all within seconds, and all without sitting at the computer and waiting through an iTunes sync. This is possible through the power of jailbreak. There's also SBSettings so that a simple swipe across your statusbar drops down a list of toggles so turning off Bluetooth is just a click away, and you don't even have to close out of your app. Adjust brightness, toggle wifi, and see your currently available ram. There's a full lockscreen dashboard that gives you access to tons of configurable widgets. It's called SmartScreen and once you've seen a screenshot, you will want it. How about playing super nintendo games, with two players, using your iphones as controllers? How about syncing your device from across the room over wifi? All this and much more are waiting for you on the other side. So by now you're undoubtedly saying "yes I want those things, but isn't jailbreaking complicated, dangerous and irreversible?" I'm pleased to say the answer is simply No. The process is soooo much easier than when jailbreaks first came about. You download a program, plug in your device, and click on 'go'. It's done in about a minute. Think you can handle that? Your data is all still there and everything syncs just like it always does. Does it take longer to boot up? No. Is there any lag on the springboard? No. Will apps randomly crash or battery life be affected? No. And if you decide you want to revert, the restore button in iTunes is always one click away. If you feel you're ready to take the plunge, here is a link to a tutorial which walks you through it in 7 easy steps. Come on in, the water's fine. EDIT (thanks to mikestoolz): All idevices use the same ssh password and once you've installed ssh you will want to change it from the default. Here's a simple guide. How to change default ssh password EDIT (thanks to lilman): For a complete, untraceable wipe of a jailbreak, follow these steps here to put your device into recovery mode: How to restore from Recovery Mode EDIT: There seems to be some concern about the fact that cydia apps don't have the same review process as AppStore apps. This is true, however, the hosts of the default repositories do test the packages they host, and with an intensely avid jailbreaking community, questionable apps are quickly identified and removed. So I recommend this: Don't add sources that you don't trust, and don't just download packages (apps) left and right without doing your research. A simple google search will tell you if the package in question has any problems associated with it. Someone who just downloads everything they see will run into trouble for sure. I hope this has helped and don't hesitate to post if you're wondering about a specific question, i'll do my best to answer.