There is a void of existing measures assessing young adults’ perceptions of childhood disorganized and controlling attachment. The current research project aimed to fill this gap by developing a convenient self-report measure, the Childhood Disorganization and Role Reversal Scale (CDRR: Meier & Bureau, 2012), which comprehensively assesses for the complexity of those attachment constructs in young adults. The CDRR is a novel measure as it assesses the unique attachment representations of mother-child and father-child relationships. This research project had three main objectives. The first objective was the development of the CDRR. It was guided by the recommendations of various scholars in scale development using classical measurement theory. The items of the CDRR were informed by the attachment and family systems literature. The factor structure of the CDRR was determined through conducting principal components analyses (PCA). The second objective, constituting Study 1, aimed to assess the psychometric properties of the CDRR, namely, its structural stability, internal reliability, temporal reliability, convergent and discriminant validity and criterion-related validity. Lastly, the third objective, involving Study 2, sought to provide further support for the validity of the CDRR. It accomplished this goal by exploring the associations of the CDRR to psychological outcomes consistent with the attachment literature, namely, problems in the separation-individuation process, unresolved feelings towards caregiver, and current psychological well-being. The results of the PCA revealed a four-factor structure for both CDRR parent versions. The CDRR mother version includes the Disorganization/Punitive, Mutual Hostility, Affective Caregiving, and Appropriate Boundaries scales, while the CDRR father version includes the Disorganization, Affective Caregiving, Appropriate Boundaries, and Punitive scales. Overall, support was provided for the psychometric properties of the CDRR. The CDRR scales demonstrated adequate structural stability, internal consistency, temporal reliability and various forms of validity. Generally, the disorganized and controlling scales were positively related to problematic separation-individuation, unresolved feelings towards caregivers and psychological problems. It is hoped the CDRR will assist researchers in broadening the understanding of psychological outcomes of disorganized and controlling attachment representations in young adulthood.