As organizations committed to providing upward social mobility and leadership development for academically high-achieving working-class youth of color, transitional school programs (TSPs) prepare students to transition from urban public schools to elite, mostly private high schools. However, TSPs' dependence on wealthy, White institutions to achieve these goals highlights racialized contradictions in the organizational field. How do TSPs navigate the race and class conflicts between the goals of their program and the racial organizational field of elite schools on which they depend for survival? Drawing on two years of ethnographic research at Ascend, a TSP in a northeastern city, this article demonstrates how because of racialized dependencies, Ascend is compelled to adopt the inequitable practices and assumptions of the racialized organizational field of elite education. Yet over time, the organization begins to resist this organizational order by decoupling their practices from elite schools. Student voice and activism contributed to destabilizing this racialized organizational order through direct action. As Ascend's loose coupling to the field became untenable during national student protests, the organization sought to recouple to the demands of student protesters by explicitly renegotiating the terms of inclusion for their students in the racialized organizational field. These findings contribute to a limited literature about TSPs, organizations critical to the desegregation of elite schools. The findings also demonstrate how studying an organization in the context of its organizational field can reveal how organizations become racialized in practice. Finally, the case of Ascend shows that decoupling, previously theorized to be a method of evading commitments to equity, may also be a method of subverting racialized dependencies.