Research on race, social class, and parent involvement in education often implies that parents' educational orientations result directly from their social class or racial group backgrounds. In this article, the authors study the involvement of working-class and middle-class African American parents. They argue that these parents' educational orientations are informed by the educational environments they navigate, their resources for negotiating these environments, and their prior social class and race-based educational experiences. Middle-class African American parents studied were more likely to select their children's schools, assess them favorably, and adopt supportive orientations toward them. In contrast, working-class African American parents studied were assigned to schools, tended to assess them less favorably, and adopted more reform-based orientations toward them. The article extends prior work by studying social class and parent involvement within the African American community and by highlighting the interaction between parents' perceptions of school context and their educational orientations.