Mexican-origin adolescent females have the highest birthrate of all other ethnic groups in the U.S. Further, teen mothers are at significant risk for poor outcomes, including low educational attainment. Therefore, examining predictors of Mexican-origin teen mothers' educational attainment was the main goal of the current study. Future-oriented beliefs such as educational aspirations and expectations are suggested to have positive implications for adolescents' educational attainment in general. Therefore, guided by bioecological, social capital, status attainment, social learning, and collective socialization of neighborhood theories, the current study examined neighborhood, maternal, and cultural predictors of 190 Mexican-origin parenting adolescents' educational aspirations, expectations, and attainment. With respect to maternal predictors, the study examined mother figures' (i.e., grandmothers') educational attainment, and aspirations and expectations for the adolescent as predictors of adolescents' educational attainment. Using a multi-informant, longitudinal analytic model, results suggest that adolescents' educational expectations, rather than aspirations, significantly predicted adolescents' attainment one year later. Additionally, grandmothers' educational attainment was indirectly associated with adolescents' educational attainment via the educational expectations of both the grandmother and the adolescent. Further, the neighborhood context indirectly informed adolescents' educational attainment via both grandmothers and adolescents' educational expectations. Finally, adolescents' ethnic identity affirmation was significantly associated with adolescents' educational attainment two years later. Implications regarding the importance of educational expectations and ethnic identity affirmation for at-risk parenting adolescents' educational attainment will be discussed.