The notion of professional boundaries is a relatively recent addition to psychoanalytic practice. Freud and his early disciples indulged in a good deal of trial and error as they evolved psychoanalytic technique. The study of these early boundary violations illuminates the study of the evolution of the concepts of transference and counter-transference. The recent publication of the correspondence between Freud and Jung, between Freud and Ferenczi, and between Freud and Jones has provided us with extraordinary insights into the boundary transgressions that occurred in the early days of psychoanalysis. The boundary violations of the analytic pioneers have contributed to the legacy inherited by future generations of analysts. Institutional resistance to addressing these difficulties in contemporary psychoanalytic practice may relate in part to the ambiguities surrounding boundaries in the training analysis itself.