Dual relationships, inappropriate self-disclosures, fee-setting irregularities, session-length extensions, and other boundary crossings punctuate this dramatic study of a psychoanalysis of an acutely traumatized patient. Describing the case from his point of view as supervisor, the author explores how overwhelming emotion, powerlessness, a wish to rescue, and a risk of ego boundary dissolution endangers psychoanalysts’ clinical methodology with such patients. Self-monitoring, self-reflection, self-caring, and training helps, but working with this population, as the case example reveals, remains a difficult, even perilous endeavor.