This book explores the changing attitudes and clinical responses to gender and transition in psychoanalysis and psychotherapy. It examines gender as a dynamic and elusive psychic situation—lived through affect, fantasy, and symbolic pressures. Gozlan argues that gender shapes experience not only in patients’ lives but also in theory—where it unsettles coherence, challenges neutrality, and brings forward what is lost or unsymbolized. Engaging figures such as Sullivan, McDougall, Stoller, and Quinodoz, he reimagines the analyst as implicated in the transmission of gendered meanings, where the mind becomes a site of ethical and aesthetic reworking. This extends to the psychic life of psychoanalytic institutions, where gender’s fate and its impact on the analyst’s own transformation are examined. The book also interrogates the conditions under which the analyst’s thinking shifts—or resists shifting—and invites readers to rethink how gender circulates through psychoanalysis, theory, and institutional life. With a deep and nuanced understanding of gender in the clinic and beyond, this book is essential reading for psychoanalysts, psychotherapists, and other mental health professionals seeking to update their thinking and practice around gender and transitioning.