Drawing on data from a longitudinal study of 204 Mexican-origin adolescent mothers, their mother figures, and their children, the current investigation examined (a) adolescent mothers' educational re-engagement and attainment beginning during their pregnancy and ending when their child was 5 years old; and (b) the influence of the family economic context on adolescent mothers' educational re-engagement and attainment and their children's academic and social-emotional outcomes. Findings detailed adolescent mothers' re-engagement in school after the birth of their child and revealed that family income during adolescents' pregnancies was directly associated with re-engagement and attainment, and also initiated cascade effects that shaped adolescents' economic contexts, their subsequent re-engagement and attainment, and ultimately their children's academic and social-emotional outcomes at age 5.