This paper looks at a clinical case in which a patient who engaged in sexual risk taking became infected with HIV in the course of his analysis. Health concerns and social stigma make contraction of HIV emotionally fraught for those infected and those close to them. Psychoanalysts working with people in this situation may find it difficult to sort through their own and their patients’ reactions, including feelings of guilt and responsibility. The paper describes the complex developmental and clinical context of one such case and shows how psychoanalytic inquiry rooted in the patient's subjective world provided a context in which the meanings of his seroconversion could be understood. This understanding allowed for emotional changes that showed promise for the patient's capacity for continued self-care.