In this brief communication, we offer one perspective – the contextual psychoanalytic supervision model (CPSM) – on how psychoanalytic supervision works. The CPSM, a supervisory extrapolation of Wampold’s contextual psychotherapy relationship model, accentuates four psychoanalytic supervisor–supervisee relationship variables as crucial and change inducing: the learning alliance bond, supervisor–supervisee real relationship, creating supervision expectations/providing an expectation-consistent form of supervision, and the supervisee’s engagement in facilitative educational actions. The CPSM is presented in hopes of stimulating further discussion about what makes psychoanalytic supervision work.