The purpose of this study was to examine the relationships among risk factors, cultural assets, and Latino adolescent mental health outcomes. We extend past research by using a longitudinal design and evaluating direct and moderated acculturation effects across a range of internalizing, externalizing, and academic engagement outcomes. The sample consisted of 281 Latino/a youths and one of their parents in metropolitan, small town, and rural areas within North Carolina and Arizona. The length of time the adolescent was in the U.S. was positively related to humiliation, aggression, and school bonding. Adolescent U.S. cultural involvement and parent culture of origin involvement were not significantly related to adolescent mental health or school bonding. Parent U.S. involvement had an inverse association with adolescent social problems, aggression, and anxiety. Adolescent culture of origin involvement was positively related to adolescent self-esteem 1 year later. Inverse relationships were found for the link between adolescent culture of origin involvement and hopelessness, social problems, and aggression 1 year later. Implications for prevention programming and policy development are discussed.