This study investigates the caregiver–child relationship as a proximal risk factor in the transactional development of youth personality pathology. 129 girls (aged 11–13 years), two-thirds of whom were oversampled for shy and fearful temperament, and their primary caregiver, participated in laboratory-based conflictual interactions. Trained observers rated positive and negative escalation, mutuality, relationship quality, and satisfaction. Concurrently and two years later, girls’ maladaptive traits were assessed via self- and caregiver-reports based on the DSM-5 Alternative Model for Personality Disorders (AMPD) domains (negative affect, detachment, antagonism, disinhibition, and psychoticism). Using a series of path models, we assessed whether dyadic interactions predicted changes in maladaptive traits. In dyads exhibiting reduced positive interaction patterns, specifically a lack of mutuality and relationship satisfaction, we observed increases in girls’ negative affect, detachment, disinhibition, and psychoticism. These patterns were more pronounced in girls’ self-reports. Negative escalation predicted girl- and caregiver-rated increases in antagonism. The study illustrates the importance of the caregiver–child relationship in the etiology of developmental personality pathology by establishing a link between observed caregiver–adolescent interactions and prospective changes in key domains of maladaptive traits. It expands the literature on dyadic interaction and developmental personality pathology to the dimensional framework of the AMPD.