The executive order process can be a long and complicated one, as directives may wind their way through various agencies before finding their way onto the president’s desk. Even after these orders have been issued, federal agencies will have a wide degree of latitude under certain conditions as it pertains to implementing them. In this article, I study the history of three separate presidential directives, two dealing specifically with environmental issues and one with general regulatory issues, in order to provide a picture of the process from inception to implementation. I consider three cases and explore the factors that drive presidents in choosing when or whether to issue an order and those that drive federal agencies to react as they do. This article encourages scholars to reconsider what they consider “unilateral,” pointing to the instances in which presidents must engage in bargaining within the executive branch they ostensibly head.