This research examined whether and how adolescents' personality traits moderate associations between psychologically controlling parenting and problem behaviors. On the basis of self-determination theory, we also examined the mediating role of psychological need frustration in the effects of psychologically controlling parenting. A cross-sectional study in two samples (N = 423 and 292; M-age = 12.43 and 15.74 years) was conducted. While in Sample 1 both mothers and adolescents provided reports of parenting and problem behavior, Sample 2 relied on adolescent-reported parenting and mother-reported problem behavior. Psychologically controlling parenting was related to internalizing and externalizing problems in both samples. Little systematic evidence was obtained for the moderating role of personality, with the exception of a moderating effect of Agreeableness. In both samples, psychological control was unrelated to externalizing problems among adolescents high on Agreeableness. Analyses of Sample 2 showed that associations between psychological control and problem behavior were mediated by psychological need frustration. Adolescent personality plays a modest role as a moderator of associations between psychologically controlling parenting and problem behavior. Frustration of adolescents' basic and universal psychological needs can account for the undermining effects of psychologically controlling parenting. Directions for future research are discussed.