Jailbreaking Apple's iOS: Thank goodness for hacking enthusiasts
Brian Dipert - June 19, 2012
-First-generation iPad
-Fourth-generation iPod touch, and
-Two iPhone 4s
from (jailbroken) iOS 5.0.1 to latest-generation iOS 5.0.1, then re-jailbreaking them. My motivation was prompted by the recent release of an untethered (i.e. no to-computer connection required for phone reboot) jailbreak for iOS 5.1.1 called Absinthe, whose exploit was subsequently folded into other common jailbreak tools such as redsn0w (which I use) and PwnageTool. And I decided that I'd better make time and take the plunge now, before Apple released an iOS update that plugged the exploit hole, and subsequently stopped signing iOS 5.1.1, thereby precluding subsequent sanctioned upgrades to it.
Thankfully, although the process was a bit tedious considering the number of devices I needed to tackle, it all went fairly smoothly. I ran AptBackup to archive a record of my jailbreak apps, then did a backup of everything in iTunes. My subsequent over-the-air iOS update attempts failed, presumably because of each device's jailbreak status, so I instead did a restore (versus an update) within iTunes, in order to completely wipe the device clean as part of the upgrade process. Note that at this point, I'd upgraded to iOS 5.1.1, but hadn't yet restored my apps and settings from backup.
I've run into problems in the past when attempting to restore Cydia apps after a restore of normal apps and settings, involving multiple GBytes' worth of storage being rendered inaccessible and labeled as 'other' in iTunes. So instead, I set up each device as 'new' and then ran redsn0w, to jailbreak it. After subsequently installing and running AptBackup to reinstall all of my Cydia stuff, I reconnected each device to iTunes and did a restore from backup to resurrect all of my other applications and settings. The only remaining (and tediously annoying) task involved re-arranging my application icons for each device, as I'd had them before. And the only glitch I've consequently encountered is that MyWi on my iPad is a bit flaky; I'm already in contact with the developer and hope that a more robust version will shortly be forthcoming.
So why bother going through this process? Below, I'll share two screens that simply but effectively make my point:

Courtesy of a jailbreak program called ShowCase, the on-screen keyboard displays lower-case letters when the virtual Shift key isn't activated. You might see this as being a nit; after all the illuminated-or-not Shift key already functionally implements this distinction. However, trust me; the notable redundancy of a lower- or upper-case keyboard dramatically improves usability.
This is just one example of many; here are others:
-SwipeSelection substantially simplifies cursor navigation, while ManualCorrect makes text correction a user choice versus an O/S insistence
-TetherMe and MyWi enable me to as-needed tether my laptop to use my iOS devices as cellular modems, without paying AT&T and Verizon extra for the privilege, and without needing to discard my unlimited-data plans in the process
-I'm able to access my devices over AppleTalk (Netatalk), SSH (OpenSSH) and VNC (Veency) protocols
-iFile provides robust file and folder management
-DisplayOut enables application-agnostic video-out to a connected computer monitor, projector or TV
-My3G allows for large-payload updates and FaceTime sessions over cellular links
-SBSettings provides for easy access to device configuration options
-SplitMail gives my iPad's email app a landscape-like interface in portrait mode, while RetinaPad noticeably improves the iPad's upscaled presentation of iPhone-only apps
-And although I don't personally do so, WinterBoard allows for extensive user interface customization
Countless other apps and tweaks are available on Cydia, for the adventurous among you. Ironically, Apple has a long history of "adopting" features that previously made their premier courtesy of the jailbreak community; I was doing application multitasking on my iOS devices long before Apple officially unveiled the feature in iOS 4, for example. And jailbreaking has also historically enabled me to add features which Apple (for technical or forced-obsolescence reasons) has declined to implement; video recording on the iPhone 3G, for example, or Siri on devices other than the iPhone 4S, or 3D mapping capabilities on my iPhone 4 handsets.
So although I realize the potential security risks of what I'm doing, I don't plan to stop. And as such, I'm both abundantly grateful to the jailbreak community for what they've accomplished so far, and hopeful that they'll be able to continue their impressive string of successes.
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