Background/Context: The term racial diversity is interchangeably used in the literature with other terms such as racially mixed, integration, and desegregation in reference to policies to design and practices to implement racially heterogeneous communities, districts, and schools. Scholarship that promotes the democratic potential of racially diverse schools argues that the policies for doing so if implemented systematically can extend equitable resources to all students and dismantle negative racial and social class stereotypes through cross-cultural interactions. However, the social justice oriented goals of a racially diverse school will never fully materialize if institutional and structural barriers as well as racial attitudes and perceptions only allow a privileged few to connect to opportunities and result in a school that is merely diverse in terms of student enrollment. Purpose: Attaining racial heterogeneity is just one goal of racially diverse schooling. Students' academic and social opportunities, engagement, and connectedness to school should also be considered. Thus, this article expands upon research that critically examines definitions of "true" diversity and calls for a policy vision for diversity that goes beyond achieving heterogeneity in student enrollment and also considers what structures and relationships are necessary to provide equitable opportunities for all students. In order to further problematize the concept "diversity", the author used Brown High School (BHS), a racially and socioeconomically diverse comprehensive high school located in a predominately White, affluent southern part of a major metropolitan area, as a critical case. The school community as a whole appreciated its racially diverse student body, but as the case study demonstrates "appreciation" for diversity did not resolve the institutional, structural inequities and racial attitudes that resegregated students of color who transferred to BHS in search of better opportunities to structures within the school that were nearly or as equally isolating as their previous racially segregated, low performing schools. Participants: Seventeen students of color were interviewed and among this sample 7 identified as Latina/o, six African American, one of Asian decent (Vietnamese), and three self-identified as multi-ethnic (Latina/Chinese, Latino/White, Latina/White). Nine faculty (the principal, two assistant principals, four teachers, one tutoring center director, and one college and career counselor) were nominated by students to also be interviewed. Research Design: This study employed qualitative case study methods to illuminate the complex relationships that unfold within the high school of study. Data Collection and Analysis: School level demographic and achievement data, observations, school documents, and field notes of student led focus groups also helped frame the high school context. All data was collected during the 2009-2010 school year. An initial round of open coding and then several iterations of focused coding were used to uncover consistent themes, issues, and story lines. Findings: The school administration unveiled a school improvement plan that would enable the school to capitalize on its growing student diversity by ensuring all students have meaningful academic and social connections to school. Despite the school improvement team's efforts to hold school community wide discussions about what changes should be made to support the increasingly diverse student body, most students of color who transferred to BHS were consigned to the lowest course and programmatic tracks, creating very disparate structures of opportunity within the high school. A complex set of factors contributed to inequities within the high school. There were vast inequities between schools across the district; thus, students of color from lower performing schools transferred to BHS already at a disadvantage in academic preparation. Also, some faculty were reluctant to change their practices to accommodate the increasingly diverse student body and harbored negative racial attitudes and stereotypes. Finally, any strategies put in place to address the inequities were very unsystematic and instead piecemeal and programmatic. Conclusion/Recommendations: In order to fully capitalize on the democratic benefits of diversity, leaders must be willing to re-organize and alter school structures so that every student is equally connected to opportunities. Also, while it is important for school leaders to engage discussions with faculty and the community about the importance of racial diversity, dialogue is only one step, as leaders must also then take action towards implementing systematic supports to address inequities. Furthermore, faculty should consider how their own racial identities and social constructions about diversity impact student experiences and make faculty dialogue about race and cultural difference an integral part of the school improvement plan. Ultimately, when racially diverse schools are not strategic about ensuring all students are connected, students of color within these settings can become even more racially isolated.