I’m Not a Mac #3–Jailbreak on the Journey from Apple: My Continuing Migration from Mac


(Graphic: A riff on the unofficial piney logo of jailbroken iPhones–now including mine. Credit: iPhone Unlock.)

This post is part of my “I’m Not a Mac” series, chronicling my controversial migration away from Apple Computer after 15 years as a Mac user. Find other entries in the “I’m Not a Mac” series archive.

I didn’t expect my Wednesday post, I Am a Future PC: Why I’m Dumping Apple after 15 Years, to garner the attention that it did. In the past two days, the post has made the rounds of several Mac headline sites and generated a lot of heated comment debate over my decision to migrate from Mac OS X to Microsoft’s Windows 7. Many of those commenters were longtime Mac users who sounded like they were taking it personally that any former Apple fan would leave the fold. While I continue on my way out the OS X door, I’d like to respond to the commenters who let me know in no uncertain terms that they don’t agree with my opinions about the Mac platform.


I could note that Macintosh is just a computing platform, not a religion, or a political stance, or a life-or-death medical treatment option. I could ask how my personal operating system preferences impact in any real way the lives of commenters who read my blog on Wednesday from many places thousands of miles away. (On Wednesday, alone, the post was read on every continent except Antarctica.)

I could point out that Apple’s requirement that Mac OS X run only on Apple-built hardware and desire for Mac users to run as much Apple-coded software on that hardware and hook as many Apple-designed peripherals to that hardware as possible eliminates choice. Sure, Apple’s applications and machines are closely integrated. Given the lack of hardware alternatives, though, they’d better be.

I could also point out that I don’t need anyone’s permission to change my OS. Numerous commenters told me they didn’t agree with my decision, my reasoning, my logic. They urged me to reconsider or at least make an argument that they found compelling. Reading these particular comments, it sounded like I needed the permission of the installed Mac user community to leave it. As if I was trying to leave a religious cult and the faithful were trying to keep me there, against my will if necessary.

But I think “tough” sums it up best. Before Wednesday, I spent several months shifting away from Apple software and over to a cross-platform or open-source software suite. In lieu of Apple’s branded Dock, software, and iApps, now I’m a regular user of Google’s web apps (Mail, Calendar, Office), Firefox, NetNewsWire, OpenOffice, DragThing, and Picasa. And I’m liking it. A lot.

Here’s where I’ve gone since Wednesday…

Linux in the Running
Several commenters suggested I give myself a wider base of comparison by trying out Linux as a potential replacement OS. So I did. I downloaded Sun Microsystem’s open source VirtualBox virtualization software, and the latest build of popular consumer Linux flavor, Ubuntu. Except for the pesky but common low resolution running in virtual mode, my initial reaction was positive. I hadn’t realized how much useful open-source software comes out of the box or is immediately available for download with Linux.

I did, however, find that I’m not a big fan of Ubuntu’s GNOME interface (one of the two main graphical user interfaces, or GUIs, used by consumer Linux builds.) So next I downloaded Ubuntu’s sister version, Kubuntu, which uses KDE, the other main Linux GUI. I think it’s a lot more attractive, but I won’t say that too loudly–the battle between GNOME and KDE users in the Linux world rivals the Mac-PC debate, and I think I’ve stirred just enough controversy this week. Besides, I haven’t yet gotten Kubuntu to play well with VirtualBox. Once I get it up and running alongside Ubuntu, I’ll spend some time trying both on for size, work-wise and play-wise.

Google Voice Rollout
Back in 2007 when I thought I wanted to move from my beloved Chicago back to my native New York City (thankfully, the urge passed), I signed up with Grand Central for an NYC-based virtual phone number to help easy my shift from city to city. Grand Central, of course, was the company offering “one number to rule them all” bought out by Google and turned into the nifty–and if you’re Apple, controversial–Google Voice service.

In my earlier post, I made no bones about wanting to shift away from iPhone and over to Google’s Android mobile phone platform. I maintain only a single phone number (it’s easier that way), so I knew a bridge number would make it easier to shift from carrier to carrier. Skype would have fit the bill, but Google Voice would work better. And lucky me, we former Grand Central users all got early access to Google Voice. (Please don’t ask for invites, I gave mine away on Twitter.)

So I laid down Google’s admittedly annoying $10 fee to change to a Chicago number of my choice and immediately contacted my friends, colleagues, and clients to ask them to ditch my old number (or as I put it, to please pet and feed my new Google Voice number and bury my old iPhone number in the backyard.) Boy, did I miss being a Grand Central user. I was happy to find most of the same neat calling features I remembered in Google’s version. Those features include visual voicemail which predated the iPhone, the ability to listen in on messages before I answer calls or to block callers permanently, and the ability to record separate greetings for different callers or groups of callers–those last three features, of course, nowhere to be found on an iPhone.

If only I didn’t have to use Google’s clunky, hastily created mobile web app to access the service from my iPhone. But, of course, I do, thanks to Apple’s ongoing, FCC-enraging refusal to allow a Google Voice app on non-jailbroken iPhones. (Can you see where this is heading?)

The Great Escape
If I was really walking away from Steve Jobs’ control over my computing life as I declared earlier this week, then I knew I had to put my money–or at least the risk of my iPhone investment–where my mouth was. Late last night, I boned up on jailbreaking procedures, read through the iPhone Dev-Team blog, downloaded the latest Pwnage jailbreaking software, and became a criminal in the eyes of Apple. All to load software of my own choice on my owned phone.

Though first I had to suffer through a common jailbreaking problem, the dreaded “1604” error. Just as  iTunes was trying to restore my iPhone from the special .ipsw file created by the Pwnage program to, essentially, break the device free from the App Store, the error popped up and my phone sat there like a sad little electronic brick.

It took an hour to figure out the problem: insufficient Pwnage documentation from the iPhone Dev-Team. If your phone has not yet been jailbroken, the Pwnage program places the phone into a deep-recovery mode called DFU mode, like REM sleep without the rapid eye movements. Once there, you restore the phone yourself using iTunes, by option-clicking the Restore button in iTunes and selecting your new .ipsw file.

Of course, the on-screen prompting in Pwnage tells you none of that, so when iTunes launched and stopped Pwnage from putting my phone in DFU mode, I followed the few instructions Pwnage had already given me once more, proceeding to put my phone into Recovery mode–not a deep enough sleep, as it were, to restore with a jailbreaking .ispw file.

This helpful site will tell you that you need to put your phone in DFU mode, and this helpful site will tell you why (unlike Recovery mode, DFU mode blocks the iBoot agent from loading, allowing for the jailbreaking magic to happen.) But, really the iPhone Dev-Team could just have said that in the on-screen instructions in Pwnage. At any rate, another hour later I had a jailbroken, fully restored iPhone, with an icon to access Cydia, the independent app store for apps Apple doesn’t want you to have. (Mind you, jailbreaking doesn’t take away access to Apple’s own App Store.)

Long story short…well, too late for that. But the time and tedium of jailbreaking was worth it for one thing: the shiny, new, free GV Mobile app that now resides on my iPhone, downloaded from Cydia. It’s the best of the Google Voice apps that Apple removed from the App Store over the summer. It integrates with my iPhone Address Book and it works beautifully.

And it uses a phone number completely out of the control of Steve Jobs. I bet that just kills him.

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