When examining the efforts of African Americans to create and operate viable primary and secondary schools from 1865 to 1870 in Kentucky, it is difficult to not contemplate what potentially might have been had national support for the Black transition from enslavement to freedom not waned. W.E.B. Dubois and several subsequent historians concluded that although the United States had the opportunity to fulfill the ideals of a democratic society during the years after the Civil War, the nation generally missed the mark when it came to African Americans (DuBois [1935] 1998, 637; Andrews 2004, 8, 29; Slap 2006, 2; Hahn 2003, 2). One area in particular where scholars have focused on this missed opportunity has been studies of segregated schools in the South during the Jim Crow era. Academics have highlighted numerous struggles, such as Black schools facing under-funding, poor facilities, the consequences of inadequate education upon Black children, and violence from White residents in the region. Others have produced works on the political roles Black educational institutions played in the post-emancipation South (Vaughn 1974, ix; Reed 2011, 2). In addition, some studies have examined the broader social impact of Black children attending educational institutions in their own communities while still others looked at Black efforts to secure education on their own terms (Walker 1996, 3; Williams 2005, 2, 69). The purpose of this essay is to examine the social significance of Black schools to the communities in which they served. A closer look at African American schools during the years following the war begs questions about how formerly enslaved Kentuckians make use of schools to not only educate themselves and their children, but also build continuity within their communities. By seeking and obtaining greater autonomy over their own schools, what obstacles did they face in their efforts to create autonomous educational institutions at a time of critical national and state political changes that occurred from 1865 to 1873?