So this is a weird one. Apple accidentally un-patched a security hole in iOS 12.4 that they'd already fixed back in 12.3, and within about a day some enterprising jailbreak developers had a working exploit out for it. As of right now, on a phone running the current, fully up-to-date version of iOS, you can jailbreak it. That basically never happens anymore. The whole story broke last weekend and I've had it open in a tab all week trying to decide if I care.
Short version for anyone who doesn't follow this stuff closely: a security researcher found a bug, reported it to Apple, Apple patched it in 12.3, and then somewhere in the process of building 12.4 the fix got reverted. Nobody's totally sure how; probably an old branch got merged back in, or someone grabbed the wrong commit. Whatever happened, the hole was wide open again, and the unc0ver jailbreak team noticed and shipped a tool for it almost immediately. Pwn20wnd (that's the handle, not a typo) had a build out that works on basically every 64-bit device from the iPhone 5s up through the XS, running iOS 12.4, the version Apple pushed out to everyone like three weeks ago.
What gets me isn't really the bug itself. Software has bugs, regressions happen, whatever. What gets me is that this is the first time in years I've seen "jailbreak the current version" be a real sentence again, and it made me genuinely nostalgic in a way I didn't expect.
I jailbroke my first iPhone back in like 2010, a 3GS, using redsn0w, and I remember it being this whole ritual — DFU mode, holding two buttons for exactly the right number of seconds, praying the tethered boot worked. This blog is old enough that I probably wrote about it at the time, though I'm not digging through nine-year-old posts to check. Cydia felt like a real app store back then, arguably a better one, with tweaks like SBSettings and Winterboard that Apple wouldn't add native equivalents for until years later. Notification Center as a pull-down shade? That was a jailbreak tweak first. Control Center too, basically.
By 2019 the calculus is just different. iOS does almost everything the old tweaks used to do. My complaints about my phone these days are things no jailbreak fixes: battery degradation, the keyboard occasionally eating a word, autocorrect being confidently wrong (it changed "ily" to "ilya" on me twice this month, which is its own kind of insult). None of that is a jailbreak problem, it's a software-getting-old-and-me-typing-fast problem.
Still, I'll admit there's a pull. Not enough to actually do it on my daily phone, because losing push notifications reliability and dealing with random app crashes for the sake of a scrollable status bar isn't a trade I want anymore. I'm not twenty-two with unlimited patience for restoring from backup at 1am on a Tuesday. But if I had an old test device lying around I'd probably throw unc0ver on it just to poke around, mostly out of curiosity about what the jailbreak scene even looks like in 2019 compared to what I remember.
The other thing worth mentioning: Apple hasn't patched this yet as of me typing this. Given how fast they usually move on stuff like this, I'd guess a fix lands within the week, maybe folded into whatever the next point release is. If you've got a device you actually want to keep jailbroken for a while, this is a pretty narrow window — update, jailbreak, and then don't touch Software Update again until you're ready to lose it. That's always been the deal with untethered jailbreaks on current firmware: it's temporary by design, because Apple controls the signing servers and once they stop signing the old version you can't even downgrade your way back into the hole.
Anyway. It's a good reminder that "fully patched and current" is a status that can quietly stop being true without anyone doing anything wrong on your end, just because a regression slipped through somewhere in a build pipeline. Worth keeping in mind before you assume the newest version number automatically means the safest one.
I'm mostly just enjoying watching Twitter get excited about jailbreaking again like it's 2012.