Disproportionate discipline has been a stubborn and pervasive problem that has affected students of color in American schools for decades. Since Congress passed the Civil Rights Act in 1964, the numbers have barely changed: Students of color, particularly Black boys, are suspended or expelled at a higher rate than their White peers. This study examines the ways that administrators at a large urban school district in the Pacific Northwest attempted to implement a policy priority aimed at reducing or eliminating the gap between suspensions and expulsions for students of color compared to White students. A case study methodology based on semi-structured interviews was used to explore how school and district leaders responded individually and collectively to achieve the policy goal without being given specific guidelines. One purpose of the study was to determine what recommendations the leaders shared as the most important for reducing suspensions and expulsions. The results suggest the racial identity and experiences of the participants affected their perspectives and practices, and those of others involved in the disciplinary process. Qualitative analysis of the interviews also revealed a number of issues contributing to discipline disparities that were not explicitly named or recognized by participants. For two years, the school district sought to reduce exclusionary discipline by setting a quantitative goal, and district data showed disparities decreased slightly. But school and district leaders were left without a comprehensive process for improving disciplinary practices, basing their actions primarily on their own experience and trainings. The study suggests that effective and detailed tools to monitor the progress of policy implementation are needed for meaningful and permanent reduction in disproportionate discipline, including clearly defined ways to promote a broad multicultural awareness that can help overcome the tendency of a school district’s organizational system to primarily promote success for White students.