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My Experiences Jailbreaking the iPad

It's been a while since I posted here (I'll add another post with links to my recent postings) but maybe this one will irritate enough people to make up for it :)


Last weekend involved more playing with my iPad and given that it’s my first Apple product since the original iPod mini, there are many things that I’d never played with. I decided that an interesting first step would be figure out why it’s so popular to jailbreak iDevices. It only took me about 30 seconds on Google to come across Spirit and the process was incredibly painless. I downloaded the app, connected my iPad and clicked Jailbreak. In a matter of minutes I had a jailbroken iPad with Cydia installed (GUI apt-get like program similar to Synaptic on Ubuntu).

Given that I spend a lot of time with Python and I’m a big fan of Metasploit and Nmap, I decided that I’d start with those apps. It was pretty impressive, to just click and install (although I did have to modify msfconsole to get it to run on its own). If I was a pentester, I’d see some serious benefits to a jailbroken iPad. However, I’m not so I continued to dig around. I had to install openssh-server and SSH into my host (there’s no terminal software for the iPad like there is for the iPhone) but that was easy enough. Now it’s time to investigate.

My biggest complaints about the iPad are:

  1. Inability to play DRM wma files.
  2. Inability to multitask.
  3. No decent text editor.
  4. No way to have portable python.

#4 was solved immediately but wouldn’t be useful without a Bluetooth keyboard and that limits the portable aspect. #1 is wishful thinking; it’s just never going to happen. That leaves #2 and #3, so we’ll explore those in more detail.

The inability to multitask is a big one for me. I’d like to have a browser and a game and email and IM open… but Mr. Jobs doesn’t want me to have that freedom. Multitasking is supposed to be one of the big things that jailbreaking gives you… I’m afraid we’ve been mislead. ProSwitcher was the first app I tried, and as soon I installed it I experienced my first stability issue… Switchboard crashed when I tried to open an app. So next I tried Multifl0w and was disappointed when the repository failed and I couldn’t try it. That left Backgrounder; which, based on what I’d read online, was my best chance. It allowed me to background applications (a partial win) however my chat still logged me off when the Window was in the background, so ultimately it was another fail. I suppose that I could have gone with full console applications, install screen and run a different console app in each window but that feels like it’s defeating the purpose of having an iPad (besides, I’ll SSH into a shell account for that functionality).

A decent text editor is something else I was excited for. I’ve recently stumbled across a source code editor in the AppStore that might solve my problems but I couldn’t bring myself to spend $10 on it just yet. In the meantime the first thought I had was ‘finally… vi’. Vi IMproved was available and I quickly installed it. It was useful but, similar to python, wasn’t overly useful without a real keyboard (the lack of ‘:’ on the main keyboard made it especially painful to use).

So all my dream iPad situations faded away but I figured I should still check to see what else was in Cydia. I have to say, I was impressed… Impressed by the sheer amount of crap that existed. I couldn’t find any useful functionality. There was software that would make the annoying mosquito sound (that’s only heard by people under 30) and software that allowed you to “shake body parts” and even software that simulated Bluetooth functionality. It didn’t give you Bluetooth functionality… It just looked like it was doing something. No software to add DUN support so that I could tether with my Blackberry. No cool office suites or useful tools, just a whole lot of useless, mindless programs.

Needless to say, my jailbroken iPad lasted less than 2 hours, at that point I did a full restore of the original OS and I’m happy that I did it. In those two hours I had the iPad crash once and Springboard about a half dozen times. I found no useful software and couldn’t accomplish any of the tasks I wanted to.

Should Python ever make it into the AppStore, even with a price tag, I’ll happily pay for it but I’m going to stick with my iPad in its default configuration. Should I ever get into pentesting, I’d probably change my mind, but it just doesn’t seem useful for anyone else to even consider.

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  1. Karsten
    June 24th, 2010 at 07:50 | #1

    I am refering to your #4 above: installing Python. I have spent 15 minutes every day to google for a short instruction how to install Python on the iPad, and couldn't find anything. I have Cydia installed and cannot find anything related to Python. Would you mind telling me how you managed to get Python on the iPad? If I can find instructions elsewhere, I'd be glad to get a link.

  2. May 9th, 2011 at 17:39 | #2

    Without jailbreaking, you can get Python on iPad with my app, Python Math.

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