Diary of a first-time jailbreaker

By Nathaniel Mott , written on February 4, 2013

From The News Desk

I should probably just put my iPhone 4S out of its misery. Its lock button doesn't work anymore; there are weird chips in the glass from me and my nephew dropping it on all kinds of surfaces; and every once in a while it does this thing where it glitches in the weirdest ways imaginable and makes me consider hermitry. That's going to change today. I've decided to jailbreak the poor thing and see if I can't get some delicious, Cydia-flavored supplements to support its old bones.

Many "geeks" or "nerds" (or whatever barely-acceptable thing it is we call people who are passionate about technology) have likely been exposed to a jailbroken device. Some even took the practice to the extreme and turned jailbreaking into a bona fide business.

I am not one of those people. To me jailbreaking has seemed like exercising or getting to inbox zero -- while it sounds nice in theory, I'm just not willing to do the work required to see any real benefit. (Yes, I know that jailbreaking has been easy for a long time. So has losing weight. Don't judge me.) Today, though... today is different. Today I finally went through with it.

This is my story. (That line best said with the "Law & Order" voice.) (Bum-bum.)

12:40pm, EST: Google "iPhone 4S jailbreak" and click on the first link -- it's from Forbes -- that mentions evasi0n, the new jailbreaking tool for iOS 6. Download the software, back my phone up, wonder why I never made the "The Titanic is syncing" joke, and start the process.

12:45pm, EST: Struggle to unlock the device and finish the jailbreak, as I thought "unlock" just meant "bring up the lock screen." Begin self-loathing and hope no one ever finds out about this even though I have every intention of writing about it later.

12:47pm, EST: Check out the finished jailbreak. Tap on Cydia, which has to prepare some file system or another and then close.

12:49pm, EST: Cydia's asking if I'm a "User," "Hacker," or "Developer." Given the difficulty I had realizing that I needed to unlock my device, I choose "User." I have officially entered the "you're in a grey legal area" land. (And probably mixed a metaphor.)

1:25pm, EST: I can no longer say that the App Store is the most frustrating piece of software on my phone. Just a half-hour with Cydia has me pining for a card view, an Apple-curated row of icons and categories, and a download process that doesn't remind me of a rooted Android phone. I've gathered that Cydia isn't always this buggy and these are just first-day jailbreak blues, but damn it, whatever happened to instant gratification?

After scouring the Web for some decent tweaks/add-ons/whatever I'm supposed to call them, I decided to go for the staples: Activator, which allows users to have their phones perform certain actions with gestures; SBSettings, which is said to do all kinds of nifty shit (sorry, didn't mean to get all technical on you there); Zephyr, which adds gestures to iOS; and maybe even an emulator or two or three.

1:40pm, EST: Look, I know it's likely just the placebo effect, but everything on my phone feels faster. Apps don't seem to take as long to load, the Springboard is more responsive, and Notification Center is something more than just a stuttery, steaming pile of crap. I wonder how long it will be until I feel like throwing the phone out a window.

Still haven't been able to install anything from Cydia.

2:59pm, EST: I watched a few Super Bowl commercials. The Audi Prom one was kinda weird, and I'm not sure that the premise -- someone who couldn't get a date to prom suddenly kisses the Prom Queen, who kisses him back -- is solid, but hey: Audi. The M&M's Love Ballad spot was pretty good too.

Oh, Cydia still won't install anything. Phone's exactly the way it was before it was jailbroken, but with the added frustration of not being able to use the service that makes jailbreaking worth it in the first place.

3:47pm, EST: Cydia managed to download part of one package -- SBSettings -- and filled me with hope just to tear it all away when things came crashing down a few seconds later.

I'd be lying if I said I'm not disappointed. After reading story after story about all of the amazing tweaks available to people who decide to operate outside Apple's ecosystem and engaging in the technological equivalent of you-know-what envy, the actual experience is pretty underwhelming, at least on the first day a working jailbreak is released.

Downloading evasi0n was a piece of cake. Getting everything to work is about as easy as backing an iPhone up to iTunes, except without all of the frustrations and rage caused by Apple's digital hub. So long as people remember what "unlocking" their device means (leave me alone!) there really doesn't seem to be any reason not to jailbreak your device and live on the edge (of your warranty).

But, at least on the first day of the jailbreak's release, there isn't really much reason to go through the process, either. There's no instant gratification, no immediate change that will help remove some of the issues associated with iOS. So far as "hacking" a product goes, jailbreaking is actually pretty... tame.

[Illustration by Hallie Bateman]