Although a majority of adolescent mothers are graduating from high school, the processes that enhance the educational attainment of adolescent mothers are not well understood. With a sample of 93 African American and Puerto Rican adolescent mothers, we assessed the effects of material support from family (i.e., child care assistance from grandmother and residence with grandmother) and emotional support from family over and above pre- and postpregnancy risk factors (i.e., maternal age at first birth, delayed grade placement before pregnancy, ethnicity, depressive symptoms, stressful life events, and repeat pregnancy) during the first year postpartum on educational attainment at 6 years postpartum. Significant contributors to the explained variance in educational attainment included: delayed grade placement before pregnancy, maternal age at first birth, depressive symptoms, emotional support from family, and residence with grandmother. Unexpectedly, higher perceived emotional support from family and living with grandmother predicted lower educational attainment. Post hoc analysis of qualitative data suggested reasons for these latter findings and point to the need to reconceptualize and broaden the elements of social support that constitute protective factors for adolescent mothers.