This study examined the relationship between supervisee attachment orientation, rapport of the supervision working alliance over time, the change of supervisee attachment orientation, and the perceived impact of supervision on the lives of the supervisees. Participants were 117 master?s level counseling student at the entry (34), practicum (45), and internship (38) levels, counseling clients with supervision. This study used the Relationship Questionnaire and the Rapport score from the Supervision Working Alliance Inventory. Data was collected via e-mail at the beginning, middle, and end of the semester. Data was examined using Two-Way Factorial ANOVAs, Bowker Tests, and Chi-Square Tests. There were statistically significant changes in attachment orientation over time, and a statistically significant relationship between working alliance rapport scores and supervisee attachment. A change in attachment from preoccupied and fearful toward secure and dismissing orientations occurred. These findings may indicate the importance of considering attachment in the supervision relationship.