This document discusses penetration testing of Apple iOS devices and applications. It begins by providing background on the Mach-O binary format used for programs on Apple devices. This format includes a header structure, load structure, and data structure. The header specifies environment information and the load structure defines memory segments. When executed, segments map bytes to virtual memory. The document then focuses on behavioral testing and security issues for iOS devices and applications. It identifies classes of issues that should be checked during penetration testing, including authentication, authorization, input validation, encryption, and more. The goal is to evaluate security across confidentiality, integrity, and availability.