This study aimed to examine Dispositional, Adaptational, and Environmental (DAE) variables at the intersection of adaptive and maladaptive personality development as a conceptual replication of the DAE-model (Asendorpf & Motti-Stefanidi, European Journal of Personality, 32(3), 167–185, 2018). In a community sample of adolescents (N = 463; Mage = 13.6 years; 51% female) hypotheses-driven cross-lagged panel models were tested. Longitudinal associations between Dispositional (i.e., neuroticism, disagreeableness and unconscientiousness), Adaptational (i.e., social problems), and Environmental (i.e., perceived quality of the parent-child relationship) variables were investigated. The results partially support the DAE hypotheses. High levels of neuroticism, disagreeableness and social problems were found to predict the perceived quality of the parent–child relationship. In turn, the perceived quality of the parent–child relationship was found to predict levels of unconscientiousness and social problems. No mediation effects were found and, in contrast to DAE hypotheses, results did not indicate bidirectional influences between dispositions and adaptations. The results shed light on differential person–environment interactions that shape personality development and the importance of the perceived quality of the parent–child relationship. These findings provide insight in pathways of personality development, that may lead to personality pathology, and demonstrate the value of the DAE model as a structured guideline that provides testable hypotheses.