Jailbreaking the iPhone 3G – Part 1 – iPhone Firmware 2.2 / OS X 10.5.6

Dev Team Pineapple

At the risk of looking like a doofus, I will admit to having had some trouble with jailbreaking my iPhone 3G.

With an array of Macs and a Windows machine at my disposal, what I thought would be rather trivial turned out to be… a tad more involved.

[Edit: However there's a happy ending, which you can read in Part 2]

 

 

A few points in summary:

- The basic idea of jailbreaking is explained fairly well here and here. Some more benefits become apparent here and some good applications available to jailbroken phones are discussed here. There’s also some good stuff at LifeHacker.  BTW, if you don’t know what it is, why the hell do you want to do it? Schnapperhead!

- The difference between Pwnage Tool 2.2.1 and QuickPwn is that Pwnage Tool gives you the option to resize your boot partition, amongst other things, whilst QuickPwn does not.

- If working from a Mac, the first step is to upgrade your iPhone to 2.2 firmware.

- Download Pwnage Tool 2.2.1 (bittorrent is your friend, links later in the post).

- Download the vanilla iPhone 2.2 .ipsw file (link later).

- Run Pwnage Tool, follow the bouncing ball to do an Expert install, up the size of the boot partition to about a gig (to allow room for applications from Cydia, the Jailbreak equivalent of the App Store).

- Have Pwnage Tool build you a modified version of the 2.2 iPhone firmware.

- Enter DFU mode as instructed, and allow Pwnage Tool to jailbreak your phone.

- Embrace the alternative lifestyle of the jailbroken…

Well, that’s the idea, and it’ll work, by all accounts, if you’ve not upgraded your Mac to 10.5.6. If you have, read on, for that’s me too. Hilarity ensues.*

 

Guides written by those smarter than me:

- Jailbreaking guide at iClarified.

- Re-enabling DFU in OS X 10.5.6, again at iClarified. My advice is to NOT do this, see later in the post for why. 

- Unlocking guide from, you guessed it, iClarified.

 

The hardware and software:

- iPhone 3G 16Gb, firmware version 2.2, Optus, unlocked by Optus a few months ago.

- All Macs (MacBook Pro (3,1), BlackBook (3,1), Mac Mini (2,1)) updated to OS X 10.5.6. with no further updates available.

- Dell D620 laptop running Windows XP SP2, with iTunes 8.0.2.20.

 

Downloaded:

- Mac – Pwnage Tool 2.2.1 – Official Dev Team torrent.

- Mac – QuickPwn 2.2 - Official Dev Team torrent.

- Windows – QuickPwn 2.2 - Official Dev Team torrent.

- Apple iPhone firmware 2.2 – Apple.com download. Do not download with Safari, it deconstructs the .ipsw file; instead, use any other browser.

- Apple 10.5.6 Combo Updater – Apple.com download. Possibly necessary if you try to muck around with re-enabling DFU in 10.5.6 by screwing around and swapping in 10.5.5 kexts.

- Note that a Windows equivalent to the Mac-only Pwnage Tool is in development; it’s called Jailbird

 

Successes:

- I have used Pwnage Tool on the BlackBook to create a customised, Pwnd / jailbroken 2.2 firmware .ipsw file, although it’s hard to tell if it’s ‘good’, ie ‘not broken’. It certainly didn’t work when I tried to restore it via the Mac or the PC. So perhaps this one’s a partial success…

 

Observations:

10.5.6 and DFU Mode – Software Workaround

- There’s a bug/feature of the 10.5.6 update to OS X that stops the DFU (device firmware update) mode working.

- Pwnage Tool requires DFU to work. Bugger.

- Tried it anyway.

- Entering DFU mode is pretty easy.
With the iPhone plugged into the computer via the USB cable, simultaneously hold down the Home and Power buttons on the iPhone for 10 seconds.
After the ten seconds, release the Power button, whilst still holding in the Home button.
Continue holding the Home button for at least ~10 seconds more, or until the device enters DFU mode.
How do you know the iPhone’s in DFU Mode?
If the iPhone screen stays blank, and odd things happen in iTunes, you’ve managed DFU mode.
If the iPhone screen blanks, but then the Apple logo comes up, you held the two buttons too long, and have simply reset the iPhone. Try again, and make sure you let go of the Power button at the 10 second mark.

- So I entered DFU mode and… the Pwn didn’t work.

- Doh!

- Supposedly, replacing a couple of 10.5.6 files with the versions from 10.5.5 is all it takes to overcome the no-DFU problem. This can be achieved by some command line hackery, or trusting in an Applescript download.

- Didn’t work for me on the BlackBook, and it seems that this is not uncommon.

- I’m still yet to convert those files back to 10.5.6 versions (a task for which, of course, there is no simple tool). I’m assuming that reapplying the 10.5.6 Combo Update downloaded from Apple will sort that out.

- [Update] After a reboot of the BlackBook, screwing around with the kexts from 10.5.5 has borked all USB. And the built in keyboard. And the built in trackpad. Which leaves very few #@$%&!!! input options. Damn. Blast.

- Looks like I’ll have to try screen sharing from the Mini. Hopefully that works, otherwise a repair install may be in order, or as a last resort, I may have to use the Time Machine backup that I made just prior to fooling about with the system files.

- Yep, screen sharing in from the Mini worked fine. Re-ran the 10.5.6 Combo Updater and all is now well. That was easy fixed, so long as you happen to have another Mac around and know how to use Screen Sharing.[/Update] 

10.5.6 and DFU Mode – Hardware Workaround

- Supposedly, plugging the iPhone in via a powered USB hub avoids the no-DFU problem.

- Didn’t work for me on the BlackBook.

- Doh!

 

Lessons Learned

- As at 21 January 2009, if you want to jailbreak your iPhone 3G, don’t upgrade your Mac to 10.5.6. 

I shall faff around some more and see what I can see. 

:(

* Not really. Maybe sympathetic chuckling.
Posted on January 21, 2009 at 16:49 by ecods · Permalink
In: Cool Kit, General Nerdery, How To..., iPhone · Tagged with: , , , , , , ,

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  1. Written by eCods.com » Jailbreaking the iPhone 3G - Part 2
    on Monday, 2 February 2009 at 13:58
    Permalink

    [...] of the issues from the previous post (Jailbreaking the iPhone 3G – Part 1) are easily resolved now that Apple has released the official 2.2.1 firmware [...]

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