Background The demographic landscape in the United States has shifted dramatically since Brown v. Board of Education, leading to more complex diversity in many school districts than the diversity contemplated nearly 60 years ago. Desegregation research has shown that countywide districts are better able to maintain diverse schools, have less White flight where enclaves do not exist, and maintain political support for high-quality, equitable schools in ways very different from the politics that exist in metropolitan areas in which city schools are separate from neighboring suburbs. While demographic diversity may provide an advantage in accomplishing integration (or allow for the possibility), as court oversight for desegregation fades, it is unclear whether the advantage of countywide districts will persist if this diversity results in more political opposition to pursuing voluntary integration. Purpose This article explores the diversity policies and politics of two countywide school districts in the South experiencing enclave growth at a time of legal and political ambiguity: Jefferson County Public Schools (JCPS) and the Wake County Public Schools System (WCPSS). Both districts’ voluntary desegregation efforts have been highly publicized as they are increasingly being affected by changing demographics and local politics. In this article, we seek to analyze how demographic change influences public support for and implementation of the districts’ diversity policies. We also examine how political debates around diversity have shifted in response to the changing legal context and enclave formation in both districts. Data Collection and Analysis Data collection in our two case study sites focuses on similar variables in each. As this article focuses on our initial investigation of the two school districts, laying the groundwork for our future empirical research, our analysis is primarily based on data collected from each school district's website describing the diversity policies, demographic data trends within the district and community, as well as information on school board representation. We also used publicly available data from local, state, and federal data sources, including the American Community Survey and the 2010 Census, media articles from local newspapers (The Courier-Journal in Louisville and The News & Observer in Raleigh), legal documents such as court filings, and policy documents from the district. Through the document analysis, at each site we examined: (1) activities by district or community leaders to promote policies aimed at maintaining diversity; (2) any legal action and/or response affecting diversity policies, particularly the development of new suburban enclaves; and (3) past, present, and projected effects of diversity policies. Conclusions Whether JCPS and WCPSS are able to achieve diversity in a time of political and legal uncertainty has yet to be determined. As demographics change, enclave schools and communities increase, politics and policymaking become more and more influenced by politically savvy parents, and the future of diversity plans remains uncertain. However, the case for and benefits of integration may be clearer than ever. The question that remains is, to what depths are school districts willing to go to establish and maintain diverse environments that are key to achieving equity of opportunity for all students.