The role of the psychoanalytic supervisor is complicated when the psychoanalytic candidate is pregnant. Pregnancy is a special event that brings a unique set of opportunities, as well as problems, into the analysis, though in the past, it was usually regarded only as an impediment. The goal of this paper is to help the supervisor of the pregnant candidate to seize the opportunities and mitigate the problems. The authors make practical suggestions about the handling of maternity leave and the complex theoretical and technical issues surrounding the question of when and how to tell the patient about the analyst's pregnancy.