When I got my iPhone 3GS, I did a jailbreak on it to have Skype working over 3G network. But with the updated Skype supporting calls over 3G, there was no need for the jailbreak anymore... A few weeks ago, after reading a bit about doing a jailbreak on the iPad 1, I was curious to see what would be possible beyond the stock iPad features. So I went to the jailbreak.me site, still running iOS 4.3.3 and after a few seconds, it was done. I have to say that i'm not a big fan of customizing and tweaking my stuff. I use them for what they can do and I am quite satisfied already. If I can change the background wall paper, that's good enough for me. I do not have the time to play barbie doll with my iPad/iPhone/laptop So, that being said, I browsed the cydia store to find the gem that was missing on my iPad. Only thing that I found useful for me was the AirPlay pluggin to enable the feature in all apps so I could play the stream on my apple tv 2... File management tools are of no use to me since I rely on Tonido for external storage. OPlayer Hd lite does a decent job at playing other movie formats but in the end, I always convert everything to mp4 format. Quality is great considering file size, can support multiple audio tracks and subtitles. Dropbox is my friend for quick sharing between my devices, but with the coming of iOS 5 and icloud, maybe I won't need it anymore... There was a pretty cool app to share the screen via vnc protocol, but is was a bit slow... Not a killer app, but it was cool. Beside that, nothing was that interesting that would keep me in the jailbreak state. iTunes is my main media server at home so all my devices can access it. I never sync, doing a backup once in a while as my emails, contacts and calendar are on google. I did check out the proposed apps on cydia for the iPad, great apps, but nothing that I could not already do. I don't care for extra gestures, new keyboard layouts or widgets. I just got used on how to do stuff the Apple way. There are some really cool tweaks available on cydia, but I think that i'm getting old as I find it more annoying to tweak than to use Cydia could be a great alternative when the device won't get any new updates from Apple. But until then, i'm quite happy with available features from Aplle. And iOS 5 will bring the last piece missing: upgrading without iTunes... Doing a jailbreak seems to provide mainly: - specific tweaks (keyboards, gestures, widgets) - file access to your device - extended customization - extended tethering possibilities (really useful if your provider is limiting/blocking the feature) - themes, themes, themes! - some close to illegal content - some unapproved apps from the AppStore But still, no killer apps that I could no find in the AppStore already... So finally, I did the upgrade to iOS 4.3.4 and got rid of the jailbreak at the same time. My 2 cents... VicoPad addict!