I'm sure that we've all experienced the chaos that a user with Administrative privileges can cause. Preventing or limiting damage, regardless of the severity, is paramount to the continued long-term survival of any organization. In this talk, I will identify some of the challenges that you are likely to face from your user community when implementing least privilege. I will also demonstrate how to identify and eliminate some types of application dependencies on privilege requirements. In a culmination of these ideas, I will show one method currently being used to automate the management and tracking of elevated privileges in a real-world environment through a variety of tools and scripts. The benefits of removing Administrative privileges far outweigh the risks, but a complete analysis of the environment and discovery of dependencies needs to be performed to help facilitate the planning and preparation of the deployment.