An educational initiative, Psychoanalytic Case Development Supervision, began as an ad hoc practical response when nearly half the candidates in a talented class lacked the psychoanalytic case required for progression. All incoming candidates were assigned a supervisor with whom to meet weekly to consider clinic applicants and patients in their psychotherapy practices for analysis. Gradually it has become clear that readying candidates, in highly individualized ways, to engage in intensive work is as important as developing patients. Not only has this program yielded beneficial results for progression; it has also contributed to a subtle paradigm shift in pedagogy centering on two contemporary controversies: objective assessment of analyzability vs. subjectivity in recommending analysis, and the value of a categorical distinction, based on frequency of sessions and use of the couch, between psychoanalysis and psychoanalytically oriented psychotherapy. A four-year process of discovery-drawing on interviews with forty-nine participants (educators, supervisors, candidates)-is contextualized within the literature on these controversies. Participants' reflections are discussed, as are other features of the program and future directions for this work in progress.