Family obligation is an important aspect of family relationships among families from Mexican backgrounds and can have significant implications for adolescents' well-being. Prior research and theory regarding youths' obligations offer conflicting hypotheses about whether it is detrimental or beneficial for adolescents' well-being. In the current longitudinal study, we used a daily diary method among 428 Mexican American adolescents and their parents to closely examine the impact of adolescents' family obligation values and family assistance behaviors on internalizing symptoms over time. The authors closely examined the role of the family context in these associations. Results suggest that family obligation values relate to declines in adolescents' internalizing symptoms, whereas family assistance behaviors are both a protective and risk factor, depending on the family context. Only when youths provide family assistance in response to acute changes in parental physical and psychological distress do family assistance behaviors relate to increases in adolescents' internalizing symptoms.