"In the field of cybersecurity there are several methodologies used to protect a system, one such is whitelisting, a mechanism which explicitly allows identified resources to access particular privileges and services, for example, a list of entities allowed when everything else is denied by default. Modern operating systems support application whitelisting management tools and provide control of access to individual users or groups at the application level. Despite the substantial amount of critical work that has been produced on system security, Windows AppLocker, though commonly used and while, over the past few years, several techniques to bypass it has been proposed, there is little automation to test its effectiveness. In addition, the majority of those techniques are scarcely documented. This dissertation conducts a study the aim of which is to demonstrate known bypasses as well as implement and document an extensible tool that can be used to automate the testing of AppLocker's configuration."