The decision about when to terminate analysis has long been underpinned by a theory-driven criterion model, which may steer the analytic dialogue away from its customary activities of free association, empathic listening, and interpretation. As a remedy to this situation, the author proposes that by paying careful attention to less consciously crafted patient communications such as dreams, the analytic dyad can consider readiness to set a termination date from a perspective that is context-sensitive and less encumbered by preordained criteria. Tracing the dreams of one analysand from the vantage point of contemporary dream theory, the author demonstrates how careful attention to the dream elucidated the patient's readiness to terminate and her complex feelings about the termination process. Finally, the author challenges the notion that the termination phase is of greater evaluative than therapeutic importance, and provides clinical material as evidence that this is not the case.