With the announcement of iOS 5 and its extensive new feature list, the first question I asked myself was of course “why would I want to jailbreak??” The decision to jailbreak or not has become more of a question of software preference, (what do you want your iPhone to do), than a necessity. I found myself drawing up a list of pros and cons, and I am seeing the reasons to jailbreak getting smaller and smaller. Even now as we find out that iOS 5 has a tethered jailbreak using the limera1n exploit (courtesy of @MuscleNerd) I have to stop and think if I should even bother.
Right from the beginning you lose one of the shining achievements of iOS 5, which is its ability to function as a standalone device. In the keynote presentation the other day, Steve Jobs announced that Apple recognizes we are getting to the point where some people may own an iPad or iPhone & never own a traditional computer. To allow these users the ability to get the full functionality from their device, iOS 5 will offer OTA (over the air) software updates. This is of course the first feature lost when you are forced to do a tethered jailbreak.
Apps like WifiSync, MobileNotifier, and others, become essentially obsolete with this upgrade, and new features such as the iTunes Match embrace the idea that Apple is listening to its customers. The “we know what’s best for our customers” attitude is what spawned a jailbreak revolution after all, and who will pay $9.99 for a Cydia app that does the same thing your device already does? We are now to the point where (in my opinion) unless you are using hacked software or tools such as SSH or VNC there is really no need to jailbreak in the first place. Add in iCloud, and the argument gets even weaker.
So the question that begs to be answered is, will you bother jailbreaking?