The Apple ecosystem continues to be an elusive yet coveted target of research. The closed nature of the ecosystem poses a high barrier to entry where even basic app analysis requires a jailbroken device. Once you are in, you are faced with a data-formats and languages used by no-one else, for which public tooling is sparse or non-existent. In this talk, we will dissect how Objective-C and Swift trip up decompilers and the analysts alike during static analysis, and how many of the encountered challenges are surprisingly easy to solve, if you know the right APIs. We will present our Ghidra Plugin where we are combining program analysis research, approximations and heuristics into a static analysis toolbox for interactive decompilation and research into the Apple ecosystem. We will discuss the technical analysis, but will also cover an often neglected facet: The UX of the actual plugin. In the end we will look at the future: What challenges still need to be solved and what features would we need from our SRE tools to more easily build solutions?