This introduction to a special issue of Psychoanalytic Perspectives proposes new terminology for a scholarly discussion of psychoanalytic supervision, emphasizing “the Supervisory Relationship” over “Supervision.” Underscoring the interactive and interpersonal dynamics of this unique collaboration, the introduction summarizes the editor’s thinking about what makes this relationship distinct, vital, and underexplored. Three interviews with seasoned and highly respected clinicians—Martin S. Bergmann, Margaret Black, and Arnold Rachman—each packed with musings and reflections from the supervisors’ side of the room, are included, as is a roundtable conversation with candidates-in-training and recently graduated psychoanalysts about their experiences from the other side of the supervisory relationship. Mary Gail Frawley-O’Dea caps the roundtable with reflections on that honest conversation. Two scholarly papers from Eric Sherman and Warren Wilner, as well as a tribute to the late Martin S. Bergmann by Mindy Utay, conclude the section.