This chapter considers the effects of differences in adolescent mother's welfare and work status, depressive symptoms, stressful life events, number of children, number of housing moves, and parenting sensitivity on their children's problem behaviors at the 6-year follow-up. It also examines the effects of the grandmother's involvement and the children's child-care experiences during the first 5 years of life on the development of these children's competence and problem behaviors as rated by kindergarten or first-grade teachers. In the New York study, the effects of differences in maternal sensitivity for child behavioral outcomes were examined using videotaped and interview data collected at several time points. Videotaped play interactions between the adolescent mothers and their children at 12 and 20 months were independently coded for sensitivity and insensitivity using the Care-Index. Younger adolescents may be more willing to defer the wisdom of their own mothers, whereas older adolescents may be more likely to believe their mothers are interfering with their parenting authority.