The centrality of the supervisory relationship to the professional development of supervisees may encourage dependency needs and regressive wishes. This process may undermine the delicate balance in supervision between an optimal didactic tension and an atmosphere of calmness and security. The present paper advises supervisors to take into account the gap in power and interests between their supervisees and themselves, and the temptation that may arise within them to use their supervisees' regression in order to avoid resistance. Such awareness will help them make controlled and appropriate use of such analytic powers and maintain the balance between supervisees' “regressive selves” and “mature selves.” In addition, a perception of supervisory relations as a space of mutual alternating regressive states is offered as an important aspect of supervisor–supervisee communication.