This paper explores the outlooks of black parents raising sons in a suburban school setting in a town that I call Rolling Acres. Dominant narratives about black males center on urban environments where hazards of violence, failing schools, and socially disorganized neighborhoods are prevalent. However, black parents in suburban settings are not immune to racial hazards when raising black boys. This article engages two domains of distinct concern for the parents of black boys: academics and social life. Through a series of in-depth interviews and participant observations with 18 families in a suburban context, I argue parents of black boys, though sometimes divided along gender lines, were concerned with a host of race-related challenges such as social promotion, special education classification, dating preferences, the stereotyping of black boys, and the strain between being cool and academically successful. These concerns demonstrate the importance of understanding how black families, and boys in particular, wrestle with the racialized and gendered power structures even in well-resourced settings. This paper adds to the emerging body on suburbia by highlighting the continued significance of race "and" gender for black residential families sending their children to suburban schools.