This longitudinal study examined whether the risk and positive factors contributing to the delinquent behaviors and internalizing problems of 454 Latino adolescents varied across maternal linguistic acculturation and adolescent gender. Although the level of cumulative risk to which the 10-to-14-year old adolescents were exposed did not vary by maternal linguistic acculturation, the factors contributing to their subsequent adjustment 16 months later varied substantially. Multiple regression analyses showed that for boys, maternal monitoring offset cumulative risk effects in the high acculturation group, but was unrelated to adjustment in the low acculturation group. Social competence served a protective function for boys in the high acculturation group, but was detrimental for boys in the low acculturation group and mother-son relationship quality directly predicted more subsequent delinquent behaviors among boys in the low acculturation group. Maternal monitoring was the only positive factor contributing to girls' adjustment, directly predicting fewer delinquent behaviors for all girls.