Let's start off with explaining one simple thing: The answer to "is iOS jailbreaking dead?" is not a yes, but it's not a no either. It's a complicated subject and the current situation is not black or white. It's grey. People have been claiming that jailbreaking is dead since the golden days of jailbreaking where devices got permanent jailbreaks thanks to public BOOTROM exploits which could jailbreak any iOS version on the device. However, as we all know, those claims were highly overexaggerated.
Or were they?
Back in 2010, when iOS 4 was released, a tool called RedSn0w was circulating. The tool utilised the BOOTROM exploits in the iPhone 3G and iPod Touch 2G and jailbroke the devices just a couple of weeks after the official iOS 4 firmware was pushed. That's when the claims of "jailbreak is dead" started popping up. Just because jailbreaking the iPhone 3GS was a tiny bit harder than the 3G, people claimed that it was too much hassle to make it worth it. Of course, people had no idea that the incredibly popular JailbreakMe.com would show up just a year later and revolutionize the whole jailbreaking scene. When JailbreakMe came out, people went crazy and jailbroke essentially everything they could. Even Apple's Demo iPhones in Apple Stores kept getting jailbroken by strangers because it was so incredibly easy.
Of course, as soon as JailbreakMe was patched, people started sounding off with the rumours once again, creating a new cycle. Every time a new iOS version was jailbroken, people were filled with joy, just to claim that jailbreaking was dead once the vulnerabilities were patched again. With the steadily increasing time that one would have to wait for a new jailbreak, the jailbreaking scene started shrinking; but not harmfully so. Some users left, but the majority stayed and enjoyed freedom on the devices they owned.
The downward spiral
When Apple launched the Bug Bounty Program in August of 2016, things started changing. Up until that point, jailbreaks were released in a timely fashion (even though some would argue about that statement). When Apple started paying security researchers to find vulnerabilities, the jailbreaking scene started falling apart. Everything we knew and loved started to shiver down a spiral of death. Jailbreak teams suddenly disappeared, Twitter accounts were abandoned, websites got taken down and everything just started going downhill.
There is very little reason for the average Joe to actually jailbreak.
There have been reports circulating that the bounty program was a failure due to low payouts for exploits and vulnerabilities. This might have been true, but it's undeniable that the same day Apple pushed the bounty program live, the jailbreak community suddenly started to rot, slowly and painfully. People started losing faith like crazy, and the only jailbreak we've seen since then has been the infamous Yalu jailbreak for iOS 10 which is so horribly buggy and unfinished that it shouldn't even be called a jailbreak. It's clearly a beta and even the official version still has a beta tag. A perfect example of people losing faith is Josh Pasholk. A dear friend of mine and a former editor at ModMy. He left us after he simply lost all faith in jailbreaking, and understandably so. After years of jailbreaking, he just... quit.
In one of mine and Jay "Saurik" Freeman's conversations, I asked him for his opinion on the current state of jailbreaking. Here is his response:
"Due to Apple having slowly fixed or mitigated many of the security weaknesses in iOS over the years, jailbreaking has become harder for the people working on exploits to develop and more complex for the users to install and manage; and, for a number of reasons, there are many fewer experts who even work on jailbreaks anymore. The result is that we don't see jailbreaks for current iOS versions very often; and, when we do, they are usually fixed quickly. Meanwhile, Apple has been adding many of the most killer features from the jailbreak community directly into iOS. This all means that there is a much smaller market of users at any time who have a jailbroken phone, in turn limiting the upside and interest for the stronger development groups to work on new jailbreak-only features, which leads to a downward spiral of interest from the community at large."
A lot of security researchers have either turned to Apple to get some kind of reward for their efforts, even if it's not a huge one, or they have simply lost interest in jailbreaking. Finding vulnerabilities has become so painful that a lot of people who actually possess the knowledge to develop jailbreaks have simply turned to other communities. Only the most faithful have stayed and sought ways to jailbreak their devices.
The jailbreaking scene has become so depressing that I don't use an iPhone as my daily driver.
The current state of jailbreaking is quite sad. It's far from what it once was and I doubt it will ever come back. Jailbreak tweaks were released on Cydia daily back in the day, with tens of packages being submitted in the timespan of just a couple of hours. Nowadays, we are sometimes comforted with unfinished tweaks that never lose their beta tag. And that's if we're lucky. This is not a stab at developers, but more at the community itself. There is so little interest in jailbreaking nowadays that people don't bother to finish their work and Luca Todesco, the creator of the Yalu jailbreak, is a stunning example of this exact thing.
Gone are the days of powerful utilities being developed for iOS. The last actual utility I've seen developed for jailbroken iOS has been NFCWriter by Elias Limneos. It's a very advanced utility that actually reminds me of the days when people unlocked true possibilities of their devices even though Apple didn't allow it.
The jailbreaking scene has become so depressing that I don't use an iPhone as my daily driver. I've switched to Android, a BlackBerry KEYone to be exact. I do own jailbroken devices, however, those are either outdated in terms of hardware or can't replace my phone as they are iPads. In order to find a jailbreakable device, you need to spend countless hours on contacting people on websites like eBay or Craigslist and suspiciously asking them what firmware their device is running. Even Freeman does not use the latest iPhone, and that is because it can't be jailbroken. He has an unopened iPhone 8 laying around his office which he doesn't even want to touch because he doesn't want to lose out on jailbreak functionality like system write access. The worst part is that for every day that goes by, finding jailbreakable devices becomes harder and harder.
Jailbreaking is not dead. It's still there for people who truly need it, like Freeman for example, but to the average Joe, jailbreaking is just not worth it. Why would Steve from across the street want to desperately try to write files to the iOS system? If he has an option to change his icons on the home screen, without going through too much hassle, he maybe will. The issue is that he does need to go through a lot of hassle so it's not worth it for him. He would much rather go the Android way and have a fairly open system straight away if that's his thing.
Jailbreaking can be compared to Microsoft's Windows Phone. It has a steadily shrinking, yet incredibly strong community. A faithful community. The whole community knows that it will end one day (or that it has already ended in the case of Windows Phone) but it stands proudly and does what it can to keep itself alive.
If you're a huge tech enthusiast who has the time and energy to spend it on jailbreaking their devices, jailbreaking is alive for you. But for the rest, it's as good as dead.
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