When medication is at play in an analysis, the nonphysician candidate or psychoanalyst faces conceptual and practical challenges, as well as countertransference risks and opportunities. A psychologist psychoanalytic candidate describes the treatment of an analysand who underwent a gradual uncovering and worsening of obsessive-compulsive and anxiety symptoms; at twenty-one months, the analysand introduced the topic of medication. These developments brought to light transference and countertransference themes connected to the analyst's status as a nonphysician candidate; conceptual and practical uncertainties about medication in the context of psychoanalysis; the complex meanings of, and indications for, medication in this case; and the ramifications of a non-physician candidate's referring a patient to a psychiatrist psychoanalyst for medication while being supervised by another psychiatrist psychoanalyst.