Transphobia, now emerging as a limit to the analytic attitude, requires the kind of psychoanalytic investigation that continues in response to misogyny, homophobia, and biphobia, as they figure in both clinical practice and theory building. Without a psychoanalytic investigation into the dynamics of transphobia in psychoanalysis, efforts to conceptualize trans subjects in an analytically open and neutral manner must falter. An exploration of the author's own efforts to overcome transphobic bias, as well as an analysis of transphobic dynamics in a well-known case in the literature, show some of the challenges that arise when attempts at thinking psychoanalytically get caught up in conscious and unconscious forms of transphobia.