Transfer of patients to interns, while frequent in training sites, is often viewed negatively. However, transfer affords positive opportunities for therapy, training, and supervision. It provides a window into patients' experiences of loss, change, attachment style, capacity for working alliance, and affect tolerance. For supervisors and interns, an opportunity exists for deeper understanding of the patient, the therapeutic relationship, alliance building and the usefulness of ongoing feedback both in therapy and supervision. Dilemmas for intern therapists include narcissistic vulnerability and sibling dynamics. With case illustrations, countertransference issues for interns and supervisors are identified and suggestions are offered for addressing transfer in supervision.