In the present research, we examined associations between contextual and individual factors and adolescents’ conflict resolution with mothers. In Study 1, we explored links between maternal responsiveness and psychological control and adolescent conflict resolution styles (positive problem solving, conflict engagement, withdrawal, and compliance) with two informants. In Study 2, we examined the unique contribution of adolescents’ personality above and beyond perceived parenting in the prediction of conflict resolution styles. Results of both studies indicated that responsiveness was related positively to problem solving and negatively to withdrawal. Psychological control was positively associated with destructive resolution styles. Study 2 indicated that extraversion predicted more problem solving and conflict engagement, and less withdrawal. Agreeableness predicted more problem solving and less conflict engagement. Finally, certain personality traits moderated associations between parenting and conflict resolution, indicating that some adolescents are more sensitive to these parenting dimensions than others.