What’s the Matter with Jailbreaking?

It’s too bad that there isn’t an easy and reliable way to maintain a jailbroken iPhone, iPod touch or iPad. That way, more people would take advantage of the things jailbreaking allows you to do. For me, one of the main attractions has been the ability to project a mirror of my iPad’s display onto a large screen — either via Display Out (as recently detailed by Chris Breen) or via iDemo (as I covered back when iDemo was called DemoGod). I still don’t understand why Apple hasn’t provided this feature as part of the iOS. For now, the only way you can do this is if you jailbreak your device. Still, jailbreaking remains an activity attempted only by a small minority of iOS users. Why is this? Two reasons.

The first reason is well-known: Apple has done its best to make jailbreaking impossible. And Apple’s best is very good. Apple maintains that jailbreaking voids your warranty and actively discourages its use. Further, Apple has modified the iOS hardware (using a new bootROM that makes untethered jailbreaks much more difficult), has changed the updating process (enforcing signature checks in iTunes, as I’ve previously described) and continues to revise the iOS software so as to block the exploits used to jailbreak. The usual result is that, with the release of each new iOS device and/or each new iOS update, any prior jailbreaking success is eradicated. For example, if you currently have a jailbroken iOS device running 4.2.1, you’ll almost certainly lose the jailbreak if and when you update to iOS 4.3. It may be months after the update release, if ever, before you can successfully re-jailbreak your updated device. Of course, Apple offers no legitimate alternative to jailbreaking. This is not a formula designed to encourage widespread adoption of jailbreaking.

The second reason may be more of a surprise: A major impediment to the acceptance of jailbreaking is the jailbreak developer/hacker community itself. They make the process more difficult to perform than necessary and make it almost impossible for the average user to get any understanding of what is going on. Some difficulty here is inevitable, given the obstacles from Apple that the jailbreak developers must overcome. But the problem goes way beyond this. Perhaps the developers don’t care about any of this. Perhaps their attitude is, if you’re not conversant in the lingo and techniques used when jailbreaking, that’s your problem. But if jailbreak developers aspire to broaden their audience, as many seem to want to do, their current approach is not helping.



A case in point is the recent release of GreenPois0n, a jailbreaking program. This release was big news in the jailbreak community; it was the first utility that could accomplish an untethered jailbreak for any and all iOS devices running the latest (4.2.1) version of the iOS. The other good news was that it did so in (for a jailbreak utility) a relatively simple manner: you connect your iPad (or whatever) to your Mac, launch the utility, follow its almost tutorial-like straightforward instructions, and you’re done.

So what’s the problem? Where to begin?

Let’s start with the name. This a minor point in the scale of things. But using the word “poison” in your name, not to mention mysteriously changing the “o” to “0,” is not designed to comfort the average iPhone user — one who is probably already a bit nervous about what risks are involved in jailbreaking.

Much worse is that, if you go to the GreenPois0n webpage, all you find are three buttons labeled Mac, Linux and Windows. Most users can probably figure out that these are the links to download the utility for your OS of choice. But it doesn’t say that. I know from experience that many users would appreciate a bit more instruction even on this basic point. More critical, the page makes no mention of what is new and significant about this particular jailbreak utility. It doesn’t even say that GreenPois0n is an iOS jailbreak utility. It goes without saying that the page offers no guidance as to how to use the utility, what bugs may still remain, what problems you may confront and how best to deal with them. Can you imagine any “normal” Mac developer marketing their software this way? It would completely fail.

While the utility’s built-in instructions are simple to follow, they still lack a level of guidance and feedback that would be welcome. For example, should your iOS device be powered on or powered off before you start the jailbreak? It doesn’t say. At some point in the jailbreak process, your screen will fill up with a bunch of text that looks like what happens when your Mac boots in single user mode. Is this normal or a sign of impending disaster? Neither the webpage nor the utility itself gives you a clue. Nowhere is there a warning that (at least with the version I tested, which apparently has since been replaced with a newer bug-fixed version) GreenPois0n may fail entirely. I had to repeat the procedure four times before I had success — and knew to do this only after reading user comments on other sites suggesting that this would eventually work.

When the GreenPois0n jailbreak fails, is your iOS device still “intact” — or is it in some unstable “half-jailbroken” state? This answer to this question, obviously of huge concern, is not mentioned anywhere. Neither is there any clear indication when the jailbreak has been successful. As it turns out, if your break has succeeded, GreenPois0n installs a utility named Loader. There is no mention of this nor any instruction as to how to us Loader. You’re apparently just supposed to somehow know that Loader’s function is to install Cydia. Cydia is the jailbreak equivalent of Apple’s App Store app — essential if you want to install any jailbreak software, such as the aforementioned Display Out. [It’s not clear to me why GreenPois0n didn’t simply install Cydia directly, rather than Loader, but that’s a separate issue.]

The Loader situation gets worse. When you launch Loader (assuming you noticed the app on your iOS device and risked giving it a whirl), you may see nothing but an almost blank screen. I once again searched the Web for help and found postings confirming this. The recommendation was to relaunch Loader several times or wait several minutes. Eventually, the option to install Cydia should appear. The problem was due to an overloaded server. In the meantime, you may inadvertently (as I sadly did) hit Loader’s option to delete itself from your iOS device. Oops. Now what? You pretty much have to install Cydia manually. I ran yet another Google search and found four different ways to accomplish this. The first three methods failed. Only the fourth one (which I found buried in a user comment at the end of an article) worked. It required running a different jailbreak utility. I was worried that running another utility on top of GreenPois0n might leave me with an iPad that would no longer boot rather than one with Cydia installed. Fortunately, that did not happen.

One positive note: A day or so later, I found a webpage that offered helpful relatively easy-to-understand advice for dealing with most of the problems I encountered. However, I doubt that potential jailbreakers new to the whole process would ever discover this page.


Other jailbreak utilities, such as RedSn0w, can be even more difficult to use than GreenPois0n. Getting started with RedSn0w requires that you “select the corresponding IPSW for your CURRENT firmware” before proceeding. However, the utility offers no information as to where to find this firmware file. It next asks you to select from options such as “Jailbreak monte” and “Just enter pwned DFU mode right now” — without any explanation as to what these options do or why you might want to choose or not choose them.

…and beyond

Some may argue that I am being too harsh in my criticism here. Some of the GreenPois0n problems were due to “opening day” jitters and have since been addressed. In any case, it may be unreasonable to expect each jailbreak utility developer to have their own marketing plan or even to take the time to document how their utility works. Still, much of what I described remains an inherent problem for jailbreaking under any circumstances. One might expect the jailbreak community to offer one or two central locations to fill in these gaps. Such a location could provide the details about how each utility works and offer advice as to which one is best to use for your circumstances. This is especially critical because, each time Apple updates the iOS, the recommended jailbreak utility (and how it works) keeps changing! In this regard, I occasionally see reference to the Dev-Team Blog. Unfortunately, this blog is written with so much jargon that it is of little use to all but the most techie of users. Happily, there are a few independent sites, outside of the jailbreak community, that do a much better job. My favorite is iclarified. It’s less than ideal, but it goes a long way towards providing essential information to novice jailbreakers. Unfortunately, as far as I know, none of the “official” jailbreak sites offer a link to this (or any other) tutorial site. You are left to find them on your own.

The way things are now, even if Apple allowed a backdoor for jailbreaking, very few people would walk through it. It’s too hard for the unskilled user to find the most basic of information: to learn which utility to use, how to use it and what to do if things (as they too often inevitably do) go wrong. Given Apple’s position, jailbreaking is not likely to ever be widely adopted. Ironically, via the jailbreak community’s own “closed” behavior, it winds up acting as Apple’s ally.