Q: My coworker has a jailbroken iPhone, and she keeps trying to convince me that I should let her jailbreak my iPhone too. My iPhone 4S is out of warranty now, but I'm still afraid of breaking it. I can't afford to replace it right now. Not that I don't trust her, but if I do it, I'd like to do it myself. Is it hard to do? Is it worth jailbreaking? Is there any chance I can get in trouble? What happens if something screws up, and my iPhone doesn't work anymore?
A: I don't blame you for being cautious. I had never tried jailbreaking an iPhone either until I received your email. I've always been a little scared to attempt to jailbreak my iPhone because I was worried it might break, too. But, I screwed up my courage and decided to give it a shot.
Is it hard to do? Not really. It used to be much harder. The first jailbreak required disassembling the iPhone! On iOS 6.0 through 6.1.2, as long as you have the most basic understanding of how to use your computer, you shouldn't have a hard time jailbreaking your iPhone. In fact, I can assume that if you are considering doing it, you probably have the skills required to do it.
Is it worth it? Well, that all depends on what you want out of your phone. If you are content with how your phone works, and you don't want to take any risks what-so-ever, then it's probably not worth it to you. However, if you'd like to try use apps that aren't allowed in the App Store, or you would like to customize your iPhone to work the way you want it to, or if you just like to tinker, you'll probably enjoy jailbreaking your iPhone.
There are fantastic customizations like alternative keyboards and themes. There are tons of great apps that you can't get in the app store, not because they have porn or have viruses, but because they work in a way that Apple won't allow. An example is an app called iCaughtU that takes a picture whenever someone tries to enter your passcode into your phone and fails. Because the app uses the camera in a way that Apple didn't design, they'll never allow that app to be sold in the App Store.
Ironically, if you want to see what will likely be in the next version of iOS, check Cydia, the app store you get when you have a jailbroken iPhone. You know how you can take a picture by pressing the volume button? Jailbreakers had that first. You know how you can double tap the home button to open another app that you were just running? Jailbreakers had that first. You know how you can change your wallpaper? Jailbreakers, well you get the point. Many of the "new" features in each version of iOS are features that jailbreakers have already had for months or years.
Is there a chance you'll get in trouble? Yes, of course, it could happen, but no, probably not, at least not with the law. The Library of Congress has said that it is legal to jailbreak a smart phone. Strangely, the same is not true about an iPad. It has to do with the vague definition of a tablet device. However, the lawyers for the movie, televison and music industry are fighting to try to change that. When it comes to the law, especially copyright law, which is what impacts this the most, what is true today could be false tomorrow. Also, you could get in trouble with Apple. As of yet, Apple has never tried to take legal action against jailbreakers, but even though you aren't breaking the law, you are breaking the terms of service that you agreed to when you set up your device. Obviously, if you do "brick" your iPhone (damage it beyond the point of repair) while jailbreaking your iPhone don't even think about taking your iPhone to the folks at the Genius Bar.
What happens if you screw up your phone? Well, fortunately, that isn't as great a risk as it used to be. If it does happen, you can usually just restore your iPhone back to its factory default settings. Don't get too excited. You could still brick your phone. But it is much safer than it was a few years ago. Jailbreaking is dangerous. It's risky. You are intentionally making something work in a way it was not intended to by the company that created it. So, in doing that, you take on all the possible risk and benefits on yourself. You're on your own, but you're not really alone because there is a whole community of jailbreakers out there that are willing to help you.
So, ultimately, I can't tell you if it's worth it. It's up to you. If you want to do it, and you're willing to take the risk, give it a shot. Check out guide on how to jailbreak your iPhone on Deemable.com. However, if you decide not to do it, don't let anyone call you chicken.