Background: Despite converging areas of research highlighting adolescence as a critical phase of reorganization of the attachment system, social cognition and the emergence of psychopathology, no published study has examined the relationship of these factors together in the context of developmental adversity. Objectives: The proposed study sought to investigate relationships between developmental adversity, attachment style, psychopathology symptoms and narrative responses to depictions of ambiguous interpersonal scenarios. Design: The study employs a cross-sectional design utilising both quantitative and qualitative data. Methods: Adolescents with known exposure to developmental adversity (N=66) were compared to typically developing adolescents (N=58) on self-report measures of attachment and psychopathology. Narrative data acquired for' each participant were coded according to a social cognition and object relations scale. The narrative data consisted of participant responses to line drawings that depicted ambiguous interpersonal scenarios Results: Results showed that compared to their typically developing peers, adolescents with a history of developmental adversity were characterized by i) higher levels of attachment insecurity ii) narratives marked by reduced representational complexity and differentiation, increased negative expectations about relationships, increased negative' affect, more attributions of hostile intent, and expectations that aggression would be poorly modulated and iii) higher levels of self-reported symptoms of current psychopathology. Further, attachment insecurity was found to significantly mediate the relationship between developmental adversity and current psychopathology. Conclusion: Results add to current understanding of the relationship between the experience of developmental adversity and attachment style in adolescence and illustrate how these factors are related to adolescents' expectations regarding ambiguous interpersonal situations. Clinical implications regarding engagement are discussed.