Homeschooling is an increasingly common schooling option for middle-class black families yet is often overlooked in research on race and education. Drawing on interviews with 67 middle-class black and white mothers living in one northeastern metropolitan area—half of whom homeschool, while the other half enroll their children in conventional school—the author examines how race influences mothers’ decisions to homeschool or conventional school. The findings show that mothers’ schooling explanations reflect their experiences as shaped by the racial hierarchy constituted in schools. Black mothers respond to a push out of conventional schools on the basis of their children’s experiences of racial discrimination. In contrast, white mothers respond to a pull out of conventional schools to individualize their children’s academic programs. Building on racialized organizations and critical race theory, these findings elucidate how the formal structure of schools is racialized in ways that constrain black mothers’ agency, while enabling the agency of white mothers to activate school choice. The findings underscore how homeschooling, often assumed to be race neutral, is racialized in ways that reproduce inequalities under school choice and appears to redress discrimination in schools.