Purpose: This article examines factors that affect school board policy making about student diversity within two southern urban-suburban school districts experiencing changing demographics: Jefferson County Public Schools and the Wake County Public School System. Both districts have a history of voluntary integration efforts, and research shows that racially diverse countywide districts can make integration more feasible. However, as courts constrain mechanisms used in policies to establish/maintain racial integration, it is crucial to examine how school boards make policy decisions while navigating the politics of their communities and competing conceptions surrounding racial diversity. Research Method/Approach: This study employed qualitative case study methods to understand under what circumstances school boards are creating policy, paying particular attention to the local sociopolitical and geographic contexts. Data collected consisted of 37 interviews with school district officials and community stakeholders. Mainstream and specialty media articles, legal documents, and policy documents from the districts or other governmental bodies also helped frame the local contexts. Findings and Lessons Learned: The two districts in our study illustrate political and legal factors that create complex environments to pursue school-level diversity even in districts with a long history of diversity policies. Our study also illustrates the difficult role of the superintendent and school boards in leading diverse communities with different histories and experiences as they navigate the local politics of diversity amid a variety of competing policy goals. We conclude with implications including the importance of remaining vigilant about student diversity efforts and perfecting technical details to minimize politicization about diversity policies.