The development of adult personality disorder symptoms, including transactional processes of relationship representational and behavioral experience from infancy to early adolescence, was examined using longitudinal data from a risk sample (N = 162). Significant preliminary correlations were found between early caregiving experience and adult personality disorder symptoms and between representational and behavioral indices across time and adult symptomatology. Significant correlations were also found among diverse representational assessments (e.g., interview, drawing, and projective narrative) and between concurrent representational and observational measures of relationship functioning. Path models were analyzed to investigate the combined relations of caregiving experience in infancy; relationship representation and experience in early childhood, middle childhood, and early adolescence; and personality disorder symptoms in adulthood. The hypothesized model representing interactive contributions of representational and behavioral experience represented the data significantly better than competing models representing noninteractive contributions. Representational and behavioral indicators mediated the link between early caregiving quality and personality disorder symptoms. The findings extend previous studies of normative development and support an organizational developmental view that early relationship experiences contribute to socioemotional maladaptation as well as adaptation through the progressive transaction of mutually informing expectations and experience.