[jammi]

I bought the first iPhone a couple of months after release, which was in August or September 2007. The first jailbreak allowing your own software to be run on one was the reason I got one. I and everyone I showed it to were blown away by what was doable with it with custom software. The CLI-only hacked SDK was pretty hard to set up and use, but it was still better than what was available for other phones.

Used it jailbroken into 2011, when I finally replaced it with an iPhone 4, which in its turn ran jailbroken until 2014. That was when I got an iPhone 6, which I'm still on and I haven't jailbroken it, because Apple more or less caught up in stock iOS with the more important jailbreak hacks around that time. It seems like iPhone 6 will be phone I'll use for the longest time, because it's still fast enough and works fine.

[jandrese]

Yeah, Jailbreaks became much less necessary over time and also harder to do. I had gcc on the original iPhone and a full build chain. It was glorious, if a bit slow and annoyingly hacky because you had to self sign everything gcc spit out before it would run.

There's only a couple of things I still miss from the jailbreak days. One was a hack for iTunes that downloaded and displayed the lyrics for whatever song you were playing. The other was a SOCKS proxy that let me tether my phone without incurring the ridiculous tethering surcharge.