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In this article, I examine the question “What are some essentials of a self psychology perspective on the supervisory process?” I subsequently make an effort to (1) identify and review self psychology supervisory materials that have appeared over the last 35 years; (2) determine the primary messages, salient themes, and crucial features that define those materials; and (3) use that resulting information to then provide a springboard for considering a more contemporary, contextualized perspective about self psychology supervisory practice. Review results are organized around two crucial areas of emphasis: (1) supervisee learning and (2) the supervisor as selfobject. The primary review conclusions are (1) supervision can most fundamentally be viewed as a disruption-construction process where the supervisee builds a practice self; (2) the supervisor–supervisee learning alliance and supervisor listening perspectives, mirroring, idealization, and empathy substantively contribute to and make increasingly likely that practice self-construction; and (3) the concept of fit now increasingly defines a contemporary self-psychology vision of supervision, where continuing collaborative effort is made to tailor an experience that best matches the unique nature of each supervisor–supervisee dyad and patient–supervisee–supervisor triad. If there is one preeminent practice principle to bear in mind, it would be this: self psychology supervision is forever energized when optimally customized and thoughtfully contextualized.