This paper adresses the challenges and paradoxes inherent to the transmission of psychoanalysis and considers some of the identification issues within the transmission process itself. First clarifying what is being sought to transmit, the author then presents three channels of transmission: the analytical experience; the theoretical experience; the supervisory experience. The latter is discussed in terms of specific challenges for both supervisor and supervisee, notably through the creation of a space conducive to elaboration. The regressive allowed by such a space demands of both protagonists a tolerance for a measure of instability affecting the boundaries of identity. Clinical vignettes illustrate these challenges. The paper also deals with the risks of idealization pertaining to the supervision process and the enmeshment of the latter with personal analysis.