The first time I jailbroke my iPhone, I almost vomited from sheer joy. After endless reboots and black screens, a pineapple with a loading bar popped up on my screen, signifying that RedSn0w had done its job. RedSn0w, for the uninitiated, is one of the countless iOS jailbreak methods which frees iDevices from the Cupertino shackles. It’s Jailbreaking, and I’m its ambivalent fan.

Why I did it: the case for Jailbreaking

I’m not ashamed to admit it, I used to be very frugal with my money. The thought of donating a dollar to Apple’s unlimited coffers made my stomach turn. Before I purchased my now sloth-like iPhone 3GS, I researched which phones had the best games and applications. Two years ago, this was the iOS platform. Today, it’s probably Android. Regardless, I wanted free shit.

Jailbreaking, like anything “illegal” is not the simplest task. I have written many articles about it and how to do it, so I won’t go into any technical details, suffice to say it’s a rush. You backup your data, wave goodbye to the artificial limitations Apple places on iOS and off you go. The best part is you can revert back to your restored data if the phone goes belly up at any point.

Initially, I jailbroke for fun. To use my phone as a memory stick, to turn my phone into a wireless router, to password protect my folders, to basically do any damn thing I please. “It’s my iPhone. I spent a fortune on it, why can’t I have full control over it?”, I told other people as I rubbed its shiny rear on my face. I was a rebel, waging a small war against Apple’s tyranny. Viva.

Eventually, I turned to the dark side of the force. A friend pointed me in the direction of an app which bypassed the official App Store, and let you downloads cracked versions of paid-for apps. Every piece of software I ever wanted was now mine for the taking.

Downloading an infinite number of apps took its toll. My phone began to bloat, weighed down by the limitations of its 16GB storage. Games such as Infinity Blade, Rage and NOVA 2 threatened to turn my once-nippy iPhone into an iBrick.

One day, my iPhone refused to reboot. Alarm bells sounded and I went to the Jailbreaking forums. “Downgrade your iOS” said some. “Restore your iPhone and jailbreak again” recommended others. “Your mom’s an android-loving whore,” some users chimed in. My life of infamy left a bitter taste in my mouth.

After one and a half years of jailbreak bliss, I decided it was time to get back to my roots. With the release of iOS 5, I resigned myself to upgrading my iPhone and forgoing my jailbroken phone. I nervously updated my iPhone via iTunes (which was more difficult than Jailbreaking, ironically) and accepted my smartphone’s fate as another digital brick in the wall. After a week of using iOS 5, I didn’t miss my jailbreak in the slightest.

Why I went back to basics: the case against Jailbreaking

Playing catch-up with Apple’s continuous string of security updates left a hole in my heart. I ached for the latest iOS features, but could not stomach having to restore, find a new jailbreak and reload my applications. I grew tired of the cycle of anarchy and oddly enough, iOS 5 brought with it enough features to ensure that my “clean” iPhone behaved the way I wanted it to.

Sure, I couldn’t customise my device to within an inch of its life, but so what? It did its job. I had WhatsApp for free messaging, emails that kept me within the office loop, Opera for browsing and finally, unobtrusive notifications.

My salary also caught up with my software ambitions. The feeling of clicking on “$0.99” and not cringing went away. I became legal. I walked down the streets with a smile on my face. I even bought Angry Birds: Seasons. How long would this delirium last?

The cloud saved me

Of everything I lost, I missed my iPhone’s ability to act as a USB drive the most. But then, the cloud reeled me in.

With the release of the iCloud last year, data become as intangible as candyfloss. My content could now be accessed from my laptop, iPad, iPhone, whatever. If data was small enough to fit on a USB drive, it was perfect for the cloud. Apple you sneaky bastards, you inadvertently took what Google (or Al Gore) created and made it even better. Touché.

Android, Jailbroken from Birth

But then there’s Android. The OS is open from day one, is endlessly customisable and has a cute robot as its mascot. The app store however, frightens me to the core.

This is why I chose Apple over Android. Apple’s app store is monitored by nothing short of a team of judges who veto apps on a whim. If an app gets into the iTunes store, you can bet your bottom dollar that it’s virus free. It may be a piece of crap, but it probably won’t damage your phone.

Android apps on the other hand, can be submitted and uploaded without fear of an Android bodyguard bouncing the bastard out of the virtual door. Sure, there is Google’s new Bouncer software but it can’t compete with actual human app aggregation.

Happy endings

We all experiment in our youth. Drugs, sex, the music of Madonna, we all crave that fix which gets our gears revving. Jailbreaking was my drug, but like all medication the high eventually wears off when reality sinks in. There will always be a means and way of Jailbreaking an iDevice, regardless of the iOS version or model, for me the thrill just faded away. But I’ll always support a free environment, the cage reality traps us in is too small as it is.