In recent decades, Congress has observed high turnover and low tenure among its staff resulting in a “congressional brain drain.” This phenomenon has raised questions as to whether Congress has adequate expertise, training, and experience to effectively conduct its constitutional and practical oversight responsibilities on the Military Health System (MHS). One way to mitigate this brain drain is to ensure Congress has available resources to bridge the knowledge gap between experienced and inexperienced staffers. This qualitative study collected data through semi-structured key informant interviews and document reviews to examine Congress’s approach to oversight of the Walter Reed Army Medical Center scandal between 2007 and 2009, including why and how oversight was conducted and stakeholder perceptions of oversight effectiveness. This study also identified lessons learned that informed the development of a Best Practices resource to help congressional staffers understand the role of Congress, the dynamics of the institution, and the art of oversight of the MHS.