The jailbreak for iOS 5, on your iPhone 4, iPhone 3GS, or original iPad seems to be ready for prime-time. The usual bleeding-edge suspects have discovered the bugs, and the Dev Team's fixed them; so now you should be ready to escape from Apple's pomaceous walled garden of parody-free, sexless, family friendliness. Here you'll find the best jailbreaking resources, in today's The Long View...
First things first:
understand the difference between a "jailbreak" and an "unlock". A jailbreak allows you to install apps from places other than Apple's App Store. An unlock allows you to use a different cellular carrier than the one blessed by your phone, and usually requires you to jailbreak the phone first. Both are perfectly legal, and jailbreaking does not encourage software piracy -- no matter what Apple PR may appear to imply.
Second:
understand the difference between a "tethered" and an "untethered" jailbreak. A if a jailbreak is said to be tethered, it means that the jailbreak is undone if you reboot the phone -- in other words, you must connect your phone to your PC or Mac to properly boot it. An untethered jailbreak is the gold standard, because you don't need to muck about with any of that nonsense.
At the time of writing, the jailbreak available for iOS 5 is tethered. If you don't understand the implications of that, then go back and read the previous paragraph!
You'll need to use a jailbreaking tool to tweak the version of iOS on your phone. You'll want the latest version of Redsn0w (0.9.9b6, at time of writing). Some Windows users have also reported success with the Sn0wbreeze tool. You'll also want iTunes version 10.5 and have already downloaded a copy of the iOS 5 install image (the IPSW file).
All the links for these and their detailed instructions are below, but first, here are some top tips, learned from bitter experience. Ignore them at your peril:
Before doing anything, back up your iPhone in iTunes.
Make sure you stop iTunes from automatically updating itself -- A long-term fear is that Apple may introduce anti-jailbreaking code into a future iTunes update, stop that software from auto-updating.
Make sure you stop iTunes from automatically updating your iPhone -- iOS updates will almost always undo a jailbreak and you may find that new updates aren't jailbreakable (at least, for a few days or weeks).
Plug your iPhone directly into a USB socket on your Mac or PC's case -- do not use a USB hub.
Unplug as many other other USB devices as you possibly can.
Use a genuine Apple USB cable, or a 3rd party cable that you know to be of good quality -- some cheapo cables can appear to work fine for regular syncing and charging, but fail in subtle ways when jailbreaking.
Be patient -- some of the steps involved in jailbreaking an iPhone take longer than you might think. If it appears to have hung, it probably hasn't. Set aside plenty of time to do the jailbreak; the last thing you want to do is interrupt it mid-process.
As ever, take care; read and understand all the caveats, both here and in the linked articles -- lest you create an expensive brick. Neither I, nor Computerworld are responsible for anything you choose to do with your iDevice -- only you are.
Taimur Asad and his colleagues are doing a consistently good job of explaining all the steps you need to take to jailbreak. Here's their guide to jailbreaking iOS 5. If for some reason you prefer to use Sn0wbreeze, here's the guide for that.
Now what? Once you're jailbroken, you should see an app called Cydia. Open that and the world of open iOS apps is yours.
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