A limited number of measures assess young adults’ perceptions of childhood disorganized and controlling attachment, and although they are empirically strong, the use of these measures can be time consuming and financially straining. The current study aimed to add to the attachment literature by developing a self-report measure, the Childhood Disorganization and Role Reversal Scale (CDRR), to assess for the complexity of those attachment constructs in young adults. This study aimed to assess the psychometric properties of the CDRR using two separate samples of 750 and 656 undergraduate students (601 females; Mage = 18.68, 66.4% Caucasian; 531 females; Mage = 18.68 years, 63.6% Caucasian; respectively), and a community sample of 96 participants (81 females, Mage = 19.27, 65.6% Caucasian). The results of the Principal Component Analysis (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. For instance, the CDRR scales demonstrated adequate structural stability (confirmatory factor analyses), internal consistency (Cronbach’s coefficient alphas ranged from .78–.95 for mother scale, and .75–.96 or father scale), temporal reliability (intraclass correlation coefficient ranged from .68–.89 for mother scale, and .69–.87 for father scale), criterion-related validity, convergent validity, and discriminant validity. The CDRR will assist researchers in broadening the understanding of psychological outcomes of disorganized and controlling attachment representations in young adulthood.