Attachment theory has established itself as applicable to many types of relationships, encompassing caregiver-child, romantic, interpersonal, and psychotherapeutic interactions. This project sought to investigate the application of attachment theory to clinical supervision. Using suggestions put forth in previous work by Watkins and Riggs, this study examined the dyadic interactions inherent in both supervision and attachment. Using the working alliance as determination of the quality of supervision, attachment styles, leader-follower attachment, and attachment-based expectations were explored as predictors for supervisor-trainee dyad outcome in a training clinic for doctoral psychology students. The study design is longitudinal and prospective. Findings indicate the necessity of measurement of supervisory-specific attachment rather than general attachment, the stability of working alliance over time, and the large contribution of the leader-member attachment framework to the understanding of supervisory attachment. Implications include the importance of maintaining hierarchical, evaluative boundaries within supervisory relationship, consistent with a leader-follower dynamic.