Although OSX has had a large gain in popularity, its underlying workings are still unknown to many. In this talk we will discuss OSX internals and how they relate to security research. Specifically, we will discuss the debugging functionality provided (or missing) on OSX, how it differs from other platforms, and the resulting state of tools (LLDB) unwieldy for many security research tasks on modern OSX. For this talk we will open source our private OSX Python scriptable debugger as a lightweight, easy-to-use programmatic alternative to the awkwardness of LLDB scripting. We will showcase the advantages of a proper scriptable debugger along with features not seen in LLDB, and demonstrate examples for vulnerability research and malware analysis.