Youth organizing within the institutional context of community-based organizations has grown exponentially. Drawing on interviews with more than eighty organizers, youth, and educators, this article examines young people's experiences as they organize to expand educational opportunities for themselves and their peers in urban school districts. The authors explore educator responses to youth organizing and analyze how race- and class-based assumptions about youth leadership, as well as differing cultural norms between schools and youth organizing groups, pose challenges for young people fighting for education reform. The authors describe three strategies youth organizing groups use to address these challenges: intensive leadership development, targeted relationship building with district administrators, and alliance building. Implications for both educators and youth organizing groups are discussed.