This is a tough question to answer as it is different for everyone. Well, let me answer some common questions about jailbreaking that might help.
What is jailbreaking?
To put it simply, hackers have found a workaround to Apple’s control of their operating system.
Why would you need to jailbreak?
A lot has been said about how controlling Apple is with what you can and can’t do with an iPhone. I believe that it is justified because it gives the user a more consistent and stable experience. Jailbreaking allows you to do things that Apple doesn’t allow.
What can you do after jailbreaking?
When the first jailbreak was released there was not even an appstore. You got the apps it came with and that was it. It was great at that point because you could get games and other apps. Now you can get just about anything with the app store and it’s over 500,000 apps. I do jailbreak still for some little tweaks that I have gotten used to.
Once you have jailbroken your iOS device, you get the Cydia app which allows you to download apps and tweaks that you can’t get through the appstore.
Is it legal?
In 2010 the US Copyright Office decided it was, but that could change soon. Read more over at Engadget.
Of course Apple doesn’t like you jailbreaking so each time a new exploit is released they try to stop it. It is a game of cat and mouse. For instance, the jailbreak hackers just cracked the iPhone4s in the last two weeks.
What is the downside?
As I mentioned earlier, Apple has it’s restrictions in place for a reason, your phone does become less stable and can be slower based on what you install.
I’ll give it a try, how do I do it?
The best way is to head over to lifehacker’s The Always Up-to-Date Guide to Jailbreaking Your iPhone, iPod touch, and iPad [iOS 5.0.1]. There is plenty of further reading there as well.
Let me know if you have any other questions or if I can help you make the most of jailbreaking your iPhone.