The supervisory relationship between psychoanalysts and dynamic psychotherapists and their supervisees has from the beginning of our history been difficult to define, because it frequently transgresses the boundaries of personal analysis and didactic teaching and learning. This article attempts to summarize the history of our approaches to supervision with particular reference to interpersonal paradigms. Clinical vignettes of supervisory difficulties for both supervisor and supervisee illustrate these approaches. Some reference is also made to cross-cultural supervision and the future of this discipline.