A walkthrough of the practice of iOS penetration testing will be covered. The basic environment, including built-in security measures of iOS, will provide a context for the talk. Thereafter, jailbreaking and the benefits of it will be discussed. This foundation will be used to build the testing environment, where various tools and techniques will be discussed – right from the basics of how to install applications. The testing methodology will be discussed on various levels - a high-level approach through to code analysis, monitoring traffic, and advanced attacks. The talk caters for both iOS developers and pentesters.