IntroductionAdolescent personality is consistently linked to behavioral strengths and difficulties. However, most of this work is limited in that it does not consider personality beyond the Big Five or economic or parental adversity contexts. The Tri‐Directional Framework of Parent and Offspring Traits and Outcomes highlights the collective influence of personality, parenting, and context on offspring behavioral outcomes.MethodsParent and adolescent cross‐sectional data were collected from 2019 to 2021 as part of the Parents and Children Together project in the United Kingdom. Adolescents (N = 310, 48.7% female) self‐reported on Dark Triad traits, parenting, and behavior. Parents (N = 288, 46.9% mothers) self‐reported on socioeconomic status and adverse childhood experiences. In two path analysis models, we examined: (1) adolescent Dark Triad, context, and their interactions as predictors of perceived maternal and paternal warmth, hostility, and control; and (2) adolescent Dark Triad, perceived parenting, context, and personality‐parenting interactions as predictors of adolescent behavioral strengths and difficulties.ResultsAdolescent narcissistic traits were the strongest predictors of perceived maternal parenting, whereas adolescent psychopathy and Machiavellianism were the strongest predictors of perceived paternal parenting. Adolescent personality interacted with contextual factors in predicting parenting, but not with perceived parenting in predicting behavior.ConclusionAdolescent Dark Triad traits, especially narcissism, and contextual factors are important for the parent‐offspring relationship and developmental outcomes. We recommend that research move beyond assessing direct trait‐outcome associations to examining how these associations operate in different environments.