Adolescence is a difficult life stage in which to navigate a transgender identity, yet adolescence plays a key role in shaping educational trajectories. While transgender-related stigma and victimization within secondary schools persists, the social climate in which transgender adolescents navigate their identity has changed over time. Analyzing data from the National Transgender Discrimination Survey, a national, non-probability sample of U.S. transgender adults, we address the following research questions: 1) Is experiencing transgender identity milestones in adolescence associated with educational attainment?; 2) Does this association vary by birth cohort? We find that those who first experienced transgender identity milestones in adolescence attained less education than those who first experienced milestones in other life stages. This association is larger among younger birth cohorts, pointing to the adolescent years as a particularly difficult time to navigate a transgender identity, even in the midst of increased transgender awareness and resources within schools and society.