This article focuses on the experiences of predoctoral interns supervising the clinical work of less experienced externs in psychology and social work as part of a training program in a large university counseling center. After 4 years of running a relationally based supervision of supervision group, the authors believe that providing supervision during internship year to less advanced trainees and being supervised on the experience is a viable approach to develop supervisory competence and a highly valued aspect of internship training. However, we have also noticed that some well-known hindrances to effective supervision may be significantly exacerbated as intern and extern struggle with their new roles as supervisor and therapist. Several examples of these interns' supervisory struggles are presented in the context of the concepts of resistance, identification, and countertransference. Naming and working through these obstacles to supervision, including feelings of rivalry that emerge between trainees who are close in professional development, are crucial to the success of these supervisory pairings.