This paper focuses on the ways in which past racial contention shapes possibilities for contemporary civic action focused on youth education. Drawing on the recently legislated Civil Rights/Human Rights Education curriculum in Mississippi—a state with an exceptionally charged history of racial contention—we identify barriers to curricular implementation in Mississippi public schools and draw on case studies of initiatives in two communities that have successfully overcome these barriers. Results emphasize how the legacies of civil rights era struggles interact with contemporary demographic and educational dynamics to enable two distinct forms of robust civic action. School-centered civic practice is enabled by communities characterized by strong civil rights organizing infrastructures, high levels of contention with White authorities throughout the civil rights era, and low participation in public schools by White families. Conversely, youth civic practice in communities marked by high levels of civil rights-era contention but significant contemporary White participation in public schools occurs through out-of-school initiatives. In both cases, however, participation in and exposure to civil rights and human rights education has occurred in racially-bifurcated ways that reflect the state’s legacy of institutionalized racism.