Update: We’ll be updating this post very soon to reflect 5.0.1.

Apple’s position was always that “jailbreaking” – the process by which users can get core control over their iPhone and install unapproved apps and services – is an illegal act that shouldn’t be allowed. Then the chief officer of the Library of Congress chimed in and state that it was purely legal and that users can do whatever they want with an iPhone once they buy it. So Apple begrudgingly accepted that decision and merely said that jailbreaking your phone “could” void your warranty. And understand this. If you choose to embark on this fun little hacking of your iPhone, you need to realize that we do not warranty, endorse or indemnify you against any calamity that may befall you. Like Apple, if you jailbreak your phone, you are on your own with the consequences. Understood? So now that the legal issues are out of the way, the question comes how, and if, one should jailbreak their phone? Here’s a few tips:

“It is also important to note that unauthorized modification of the iOS is a violation of the iPhone end-user license agreement and because of this, Apple may deny service for an iPhone, iPad, or iPod touch that has installed any unauthorized software.”

 

1. Should you?

The first step in jailbreaking your phone is to ask yourself if you should? The only real reason to jailbreak is to install an app that isn’t available on the iTunes App Store. But recently, someone has accomplished porting SIRI to a jailbroken iPhone 4, and 3S. With Apple having no immediately plans to offer SIRI onto older generation phones, there may be a good reason other than Apps to jailbreak the phone. There used to be that tethering was a good reason, but now most carriers offer tethering at a price. So, unless you’re trying to avoid a monthly charge – which could end up on your bill if you jailbreak anyway, the real question is, it it worth it?

2. Consider the Risk

While most of the danger in jailbreaking your phone has largely been eliminated, there is still a chance that attempting a jailbreak will end up rendering your phone non-operational (bricking it). And Apple has stated that jailbreaking your phone does void the warranty. So you’re on your own should something go wrong. But even if the worst case scenario happens and your phone does get into a bricked state, there are ways to bring it back to operational function.

Mostly, though, many have reported that their worst case scenario was some apps don’t really work right after the jailbreak, and you will certainly not be able to update your phone with new software from Apple while it is in jailbroken condition. However, with a simple hard reset, your phone is back into it’s sand-boxed condition, and then you will be able to upgrade it with any software updates. Just don’t try and update it without resetting and wiping out the jailbreak.

3. Back up your phone

Before you do anything. BACKUP. Not only to iTunes, but also to the cloud. That way should anything back happen, your data, songs, and apps are safely backed up. Also, back up to iCloud. This is fairly simple by going to Settings>iCloud>Storage and Backup>Backup now.

4. Choose your poison

There are several ways to jailbreak an iPhone. Perhaps the easiest is to go to jailbreakme.com from your mobile Safari browser. Jailbreak Me is the simplest way to jailbreak an iPhone with just a simple step. Tap on the Free button under Cydia and then tap on the Install button, this should jailbreak your iOS device and install Cydia (as seen in the screenshot below) just like installing an iOS app from the App Store. It is as easy as that.

Another option is to go with an app called Redsn0w and follow these simple steps:

1.  This jailbreak will require you to connect your iPhone to your PC and then install RedSnow to your PC.
2.Then you run Redsn0w on your PC and click on “patch.” This will patch your iPhone to accept the Cydia Store app. You can also add multi gesture functionality and a few other features.
3. Then you will follow the direction to go into DFU reset mode (top button for 3 seconds, then home button) and reboot your phone.
4. RedSnow will then use a utility called LimeRain to jailbreak your phone and install Cydia. Do not touch it at this time.
5. Once done, you need to exit and turn off your device.
6. Then, in the RedSnow desktop utility, select “just boot” and turn on your device by entering into DFU mode again according to instructions. Once that’s done, the iPhone is jailbroken and will reboot.

There are others including BlackRain, GreenPoisOn, PwnageTool and SnowBreeze and each has it’s own directions on how to jailbreak. The best thing to do is to spend some time over at the iPhone Development Team Blog for more information on each.

UPDATE:  The iPhone Development Team has recently released a new version of Redsn0w, vs. 0.9.9b8, that can not only jailbreak iOS 5.0.1, but also has some of the Pwnage tool functionality built right into it.  For more information, check out this blog post for update 16, which contains updated versions of the software for each platform, Mac and Windows.  But one thing to keep in mind … this jailbreak is still tethered, with IDT working on an untethered option.  Those who choose to jailbreak now, will not be able to downgrade to iOS5.0 to try the untethered option once it’s out, meaning once tethered, it may be the end of the line for you.

5. Understand your limitations

As I mentioned previously, with a jailbroken iPhone, you cannot just update your phone anytime Apple release and update. To do that, you have to reformat and reset your iPhone back to it’s factory condition. But the iPhone is also more open to exploits and attacks when jailbroken. Granted, it’s largely theoretical, but it can happen. You can guard against this somewhat by changing the root iPhone password. Root Click on the Password How-To button in Cydia to learn how. But if you forget the new password, you’re stuck.

Also, you’re battery life could suffer from unapproved apps that aren’t well tested and can leach power from unclosed services. Additionally, those apps may be unstable which could cause your iPhone/iPad/iPod to reboot or crash.

And depending on what phone/OS you have, a jailbreak may not be possible, at least in the short term. But time is on your side and sooner or later, even the most recent update gets Jailbroken. And then you have to go through the process all over again.

6. Wrapping up

So, after all that you have to ask yourself the first question again … is it worth it? Frankly, I don’t think so. Unless you have a very limited need to jailbreak, there really isn’t anything that Apple has addressed with an update or a new app (and there are over a half million now). In the end, jailbreaking may be a fun exercise, but one that will largely give you a pyrrhic victory over Cupertino.










James DeRuvo