Drawing from an ethnography, this paper evaluates the motivations of Black American and Black immigrant parents when selecting high schools for their millennial teenage children in a segregated city and suburbs of New York. Black middle class parents encounter racial exclusion in the areas of work and residence. However, more research is needed to understand how they negotiate segregated schools. Analysis of interviews with 60 Black middle class parents suggests that choosing schools reveals parents' strategies of intergenerational mobility for their Black children. Urban parents believed that contact with a racially diverse student body was a key indicator of school quality. Black American suburban parents who chose their local school exhibited faith in the curricular diversity of public schools, while immigrant parents believed in the superiority of a private school education. This pattern exacerbated the economic vulnerability of immigrant families who pay high tuition costs in an already high tax suburbs. These findings demonstrate how racial inequity, class precarity, culture and space shape how Black families navigate the moving target of educating their children.