It's official. I give up. I am no longer jailbreaking my iPhone.
I am aware that, by itself, this is not especially earth-shattering news. In the larger scheme of things, how I use my iPhone is of small consequence. However, I have long been an advocate of jailbreaking, citing the advantages of helpful software that is otherwise forbidden in the App Store. I have emphasized that the risks of jailbreaking are small and recoverable. And I have lamented Apple's position, arguing that my iPhone should be just as open as is my Mac.
Given all this, I figure that if I am ready to give up on jailbreaking, there are probably many others that will soon be making (or have already made) the same decision. That's why, barring an unexpected shift in the equilibrium, I expect jailbreaking to play a declining role in the future of the iPhone.
Why have I made this decision? Because, while there are still benefits to jailbreaking, the cost-to-benefit ratio keeps increasing. I'm not talking about any single big change here but rather the accumulation of many tiny cuts. With each new cut, it becomes harder to make the case for jailbreaking. To borrow another metaphor, there are now enough straws on the camel's back to break it.
The most recent straw came from the revised "iPhone Developer Program License Agreement," which (as noted in this ars technica article) specifically prohibits App Store developers from supporting or contributing to jailbreaking in any way. This is not a big surprise. As I previously covered, Apple has already argued in court that jailbreaking is illegal. As such, it only makes sense that Apple would seek to prohibit developers from engaging in such activity. While I doubt that this move will completely eradicate jailbreaking (which, by its very nature, depends upon people who snub their noses at such legal restrictions), it is certain to reduce the ranks of what is already a minority group. This, in turn, will reduce the quantity and quality of jailbreak software, making jailbreaking itself less and less worth the effort.
By itself, even this would not be enough to convince me to abandon jailbreaking altogether. The problem is that there are numerous other hassles (mostly stemming from Apple) that a jailbreaker must endure.
For starters, every time you install an update to the iPhone software, no matter how minor, you can expect to have all your jailbreaking software deleted. This means, that with every update, you pretty much need to start from scratch — redoing the jailbreak and reinstalling the deleted apps. In addition, it's likely that all your standard synced information and media will be removed, forcing you to do a time-consuming resync to get them all back on your iPhone.
Once you have gotten past these hurdles, you may find that some of the jailbreak apps that worked under the old iPhone software no longer work. The only potential fix here is to wait for the release of updated versions of the relevant jailbreak software. In some cases, the developers give up, meaning that the updated version will never appear. Which means you are out of luck.
Beyond all of this, there is the question of whether or not the iPhone can even be jailbroken immediately after an iPhone OS (or even a Mac OS) upgrade. With some luck, a working jailbreak may be available upon release of an iPhone update. For example, the iPhone Dev-Team claims to have already jailbroken the as-yet-unreleased iPhone 3.0. Whether or not this is still the case by the time the 3.0 update arrives remains to be seen. In the past, delays of days or even weeks have been common. The second generation iPod touch proved especially difficult to jailbreak. As I recall, it took several months before a solution was found.
On a related note, after Mac OS X 10.5.6 was released, some jailbreakers found that the iPhone's "DFU mode" (needed to jailbreak) no longer worked. Various solutions were offered, such as connecting the iPhone to a Mac via a USB hub rather than connecting the iPhone directly.
All of these hassles have worked to up the "cost" of jailbreaking.
Further hovering over jailbreaking is the ever-present danger that the next release of OS software or the next generation of iPhone hardware will render jailbreaking all but impossible.
Finally, although the risk is small, there is still some chance that a glitch in the jailbreaking software could bring down your iPhone, annoyingly forcing a restore. Should even a restore fail, you may really be up-the-creek, as Apple will not help you "fix" a jailbroken device.
Coming from the other direction, the range of software that is readily and legally available from the App Store (much of it free!) continues to grow — thereby further reducing the advantages of jailbreaking. True, there are still features not yet available for the iPhone (and, so far, not slated to appear in iPhone 3.0) that I would like to see. And many of these features can already be added via jailbreaking (such as nested folders in the Home screens or video recording with the Camera). However, these are not ideal solutions. Too often, the relevant apps feel like an awkward kludge compared to Apple-implemented features.
Taking all of this together, it just made sense to give up on jailbreaking. With all the risks, hassles, and crude buggy software, jailbreaking no longer seemed worth the bother. I still have an old iPod touch that I jailbreak for testing purposes. But I no longer jailbreak any iPhone or iPod touch that I depend upon for "real world" use.
Ultimately, this decision is a compromise, one that I am less than overjoyed about making. I especially miss one critical category of software, which remains sadly absent from my jailed iPhone: apps that provides direct access to the iPhone drive and its OS files. I'm especially talking about apps such as Terminal and Finder. With these apps, I could access items (such as .plist files) that permit the sort of troubleshooting fixes that are essential on a Mac, and would be just as worthwhile on an iPhone. Related software allowed me to mount the iPhone as an external drive, making it easy to access iPhone files from my Mac and, if needed, transfer files back and forth between the Mac and iPhone.
If Apple would permit just these programs, I would happily give up on jailbreaking in an instant, with almost no regret. Sadly, such software is probably at the top of the list of apps that Apple seeks to keep out of the hands of iPhone users. From Apple's viewpoint, blocking these programs is essential to maintaining the iPhone as a "closed system." So I am not optimistic here.
In the end, I expect jailbreaking to remain as an option for those minority of users who have more tolerance for its hassles than I do. I wish them well. For the rest of us, all we can do is make the best of what Apple provides and keep pushing for them to provide even more.