The articles in this special issue examine the increasingly complex relationship between segregation, desegregation, and integration in a sociopolitical environment vastly different from that of the initial days of desegregation. These issues are examined from historical and political perspectives, contextualizing the complexities of segregation, desegregation, and integration in the twenty-first century. The articles challenge school leaders to critically engage in pioneering processes within their communities that work to create, maintain, and sustain diverse schooling environments.