One of the most critical steps of any security review involves identifying the trust boundaries that an application is exposed to. While methodologies such as threat modeling can be used to help obtain this understanding from an application's design, it can be difficult to accurately map this understanding to an application's implementation. This difficulty suggests that there is a need for techniques that can be used to gain a better understanding of the trust boundaries that exist within an application's implementation. To help address this problem, this paper describes a technique that can be used to model the trust boundaries that are created by securable objects on Windows. Dynamic instrumentation is used to generate object trace logs which describe the contexts in which securable objects are defined, used, and have their security descriptor updated. This information is used to identify the data flows that are permitted by the access rights granted to securable obj...