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This article discusses the three versions of Winnicott's most well known paper ‘Transitional objects and transitional phenomena’ published in the Collected Works of Donald Winnicott (2016) and traces the development of his ideas over a 20-year period. It describes the changes in emphasis, the early inclusion and later exclusion of references from child therapy, and notes other omissions that contribute to a change of emphasis. It discusses the addition of two clinical cases in the text of the final version, which together with the introduction of the notion of ‘paradox’, demonstrate the shifts in Winnicott's own thinking following on extensive clinical experience and lively debate. The article argues for a different assessment of the meanings of the transitional object and the much more extended interest in transitional phenomena that emerges in line with Winnicott's own claim that Playing and Reality, his last book published posthumously, taken as a whole, constitutes a discussion of the significant theoretical and clinical implications of attention to transitionality and transitional phenomena as proposing a shift in the understanding of the analytic session, the analytic process and what analysis does.