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Introduced by Fleming and Benedek (1964, 1966) half a century ago, the learning alliance has since become widely accepted as crucial for and pivotal to effective process and outcome in psychoanalytic supervision; it is now generally viewed as being the very foundation and touchstone for the totality of the supervisory experience. In this article, I consider how the learning alliance has evolved across its first 50 years, (a) becoming more democratized, relationally focused, mutual, and collaborative in its implementation, (b) reflecting a far less pathologized and pathologizing perspective on supervisees, and (c) incorporating a far deeper appreciation of difference and diversity across the supervisory triad. I also identify a couple of pressing needs that, if pursued and addressed, could contribute substantially to our knowledge base about the learning alliance: (a) vigorously initiating a program of psychoanalytic supervision alliance study, both qualitative and quantitative in nature; and (b) complementing and integrating our understanding of the learning alliance with theories of learning/instruction and educational psychology. Although the learning alliance has “grown” in accordance with relatively recent changes in psychoanalysis and psychoanalytic supervision, this 50-year retrospective also bears testament to the enduring nature of Fleming and Benedek's contribution and celebrates the seminal and promethean effect of their work on psychoanalytic supervision today.