This talk aims to give a general overview of iOS Jailbreaking by starting at what jailbreaking was back in the days and how it evolved up until today, while also taking a quick look at how it might evolve in future. Therefore the following topics are covered: - Jailbreaking goals (technical) - Types of jailbreak and it's origins (tethered, untethered, semi-tethered, semi-untethered) - Exploit mitigations (ASLR, iBoot-level AES, KPP, KTRR, PAC) - Kernel patches (h3lix) - Kppless jailbreaks The goal is to give an insight into the jailbreak terminology, exploit mitigations and how these are dealt with in past and modern jailbreaks.