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Having now completed its first century, psychoanalytic supervision has been and continues to be regarded as the cornerstone of psychoanalytic education; it is the primary means by which (1) psychoanalytic ideology becomes translated into practical product, and (2) budding analytic practitioners develop and grow in their therapeutic skills and professional identity. The supreme significance of supervision in contributing to the making of the competent psychoanalytic practitioner now seems a widely accepted given, even axiomatic. But as its second century gets underway, what have we learned from psychoanalytic supervision's first 100 years? What are its most pressing needs and, in turn, impressing possibilities at this time? And what needs to most change if psychoanalytic supervision is to most profitably advance in the years and decades ahead? In this paper, I would like to consider those questions, giving focus to five needs that seem to most require attention now: (1) making the practice of psychoanalytic treatment an increasingly competency-based, concretized learning affair; (2) enhancing the efficacy of supervisors through competency-based practice and training in psychoanalytic supervision; (3) more effectively incorporating existing technology and emerging technological advances into supervision and using them to enhance the psychoanalytic learning process; (4) better attending to matters of difference and diversity, and striving to seamlessly integrate them into the conceptualization and conduct of the psychoanalytic supervision experience; and (5) vigorously researching the psychoanalytic supervision process and working to establish an evidence base for supervisory practice.