A diathesis-stress interaction model is used to describe multifinality in adolescent internalizing and risky behavioral outcomes. Problematic behavior associated with adolescent insecure preoccupation (a diathesis) was expected to interact with the level of maternal autonomous discourse (a stressor) to predict specific adolescent outcomes. Assessments of adolescent preoccupied attachment organization, observations of maternal displays of autonomy in mother–adolescent interactions, and adolescent reports of internalizing symptoms and risky behaviors were obtained at age 16. As predicted, maternal autonomy in the mother–adolescent relationship helped to explain multifinality in dysfunctional symptoms among preoccupied adolescents. Adolescent preoccupation was more strongly linked to internalizing behavior when mothers demonstrated low levels of autonomy in interactions with their adolescents and more strongly linked to risky behavior when mothers displayed extremely high levels of autonomy. Implications for autonomy processes in increasing our understanding of how adolescent insecure–preoccupation relates to profiles of specific problems during adolescence are discussed as is the importance of exploring the role of attachment in different contexts.