As months of frenzied iPhone rumors are put to rest, a nagging question remains. For iOS users like me who have jailbroken their devices, the debate begins: Should I upgrade to iOS 6? Would having an iPhone 5, which ships with the new iOS version, be worth giving up the advantages I now enjoy? For many jailbreakers, these answers are no-brainers, but for me they pose something of a dilemma.

Jailbreakers enjoy a host of unauthorized apps and OS tweaks from the Cydia app store. For us, upgrading to a new version of iOS means losing our phones' jailbroken status. That is, until developers come up with a new hack. After iOS 5 launched, we waited for two months for the first untethered jailbreak (that is, one that didn't require connecting the phone to a computer for each reboot), and even that didn't cover devices with the A5 processor like the iPad 2 and iPhone 4S. A month later, the Absinthe A5 tool was released, liberating the newest Apple gadgets. 

Weighing the Pros and Cons of Losing the Jailbreak

Three months might not seem like a long time, but it can be a painful period of living without the features and tweaks that Cydia affords. Of course, the wait this time will depend on how aggressively Apple patches the exploits that allowed developers to crack open iOS 5 and whether the new A6 processor throws up another roadblock to jailbreak developers. 

The decision of whether or not to upgrade next week depends on how heavily you rely on Cydia's apps and tweaks. I'm a casual jailbreaker myself, but I do like the freedom it enables. For me, upgrading is a tough call, but one that might be easier to make once I've had a chance to play around with iOS 6 on my iPad first. 

For some users, things like data tethering (without paying a carrier) will be hard for to live without, especially when they cost only a few bucks to install. Much of what's available in Cydia, though, is relatively inconsequential. Can you live without the ability to add a fifth icon to the dock, rename apps and reskin the OS? That depends on how badly you want to try the new Maps app, redeem tickets and coupons with Passbook, and take the other 200 new features of iOS 6 for a spin. If you're mulling over a hardware (rather than strictly OS) upgrade, the iPhone 5's faster processor, taller screen and 4G LTE connectivity factor into the decision. Are those things more exciting than the ability to play Super Mario Bros 3 in an old-school NES emulator and customize your phone? If so, go ahead and preorder the iPhone 5. 

Apple has a tendency to borrow generously from jailbreak developers, so some jailbreak features won't be lost at all. Using FaceTime over 3G, for example, is now a standard feature in iOS. 

So much of this conundrum is a matter of digital lifestyle. Many people like tricking out their Notification Center with tweaks and widgets, and for that, tools like SBSettings and IntelliscreenX are invaluable. I've grown accustomed to using Sparrow as my default email client and Chrome as my default browser.  Other things, like the custom design theme I'm using and various minor visual tweaks, aren't of dire importance to me.  

Still, I like having more options than the average iPhone owner. Even if I'm not tricking out my jailbroken iPhone with every bell and whistle, it's nice to know I have the freedom to do so.