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Despite general agreement as to the importance and subtlety of managing the final (“termination”) phase of psychoanalysis, the way that analytic work is brought to a close has been both undertheorized and problematic in practice. How and under what conditions a psychoanalytic process might best be brought to an end is a problem that has plagued psychoanalytic theorists, clinicians, and their patients from the earliest days of psychoanalysis. Patient and analyst do not discover a “royal road” to the end of analysis. Rather, patient and analyst together forge a trail through the thickets of their work to a juncture at which they find that their paths can once again diverge. This paper attempts to explore the ways in which patients and analysts negotiate these most complex and elusive transitions. Analyst and analysand, having come to recognize the limits of their conscious awareness and the ultimate uncertainty at the heart of the psychoanalytic process, must live with the tension generated in the encounter between the inherent limits that eventually will herald the end of analysis and the recognition of new possibilities that beckon the pair into new byways of analytic exploration. Since we can never be certain when ending analysis forecloses promising avenues of new growth, or when continuing analysis constitutes a collusion between patient and analyst in eluding the difficult but ultimately generative ending of analysis, the author suggests that it is preferable to hold the notion of termination lightly, trying as best he can throughout an analysis to facilitate the exploration of its very boundaries, limits, and possibilities.