The author discusses perspectives on gender formation or diagnosis focusing on ideas from transactional analysis, post-Jungian thinking, and aspects of psychoanalysis to illustrate approaches to working with the emergence of gender. The development of gender is contrasted with viewing it as a biological given. The therapist’s role and the aim of therapy with people who identify with a gender that differs from their assigned gender (gender dysphoria) is considered. A case study illustrates dynamics in this work that can be confusing and confrontative for both client and therapist. In the struggle to provide a solid holding frame, the author suggests that gender diagnosis benefits from supporting clients’ development toward living comfortably and safely in their bodies.