Pregnant and parenting adolescents are at significant risk for educational underachievement. Educational expectations play a critical role for understanding subsequent educational attainment; yet, limited empirical attention has been given to changes in educational expectations across the transition to parenthood among adolescent mothers. This longitudinal study explored stability and change in educational expectations across the transition to parenthood among 191 first-time pregnant Mexican-origin adolescents (M _age = 16.76, SD = .98). The current study also examined how several contextually relevant risk and protective factors were associated with differential patterns of educational trajectories across this transition and subsequent educational attainment. Latent class growth analyses revealed three educational expectation trajectories: low and stable (< high-school degree), moderate and increasing ( associate degree), and high and increasing ( bachelor’s degree). Adolescent mothers in the low and stable group encountered several educational risk factors that partially explained their probability of membership in this trajectory and subsequent lower attainment. Conversely, probability of membership in the high and increasing expectations class was partially explained by adolescents’ on-track school status at the time of pregnancy and their mother figures’ educational expectations for their pregnant daughters. These findings have implications for understanding the malleable factors that help to explain why some adolescent mothers describe consistently high educational expectations and subsequent higher attainment, while others do not.