This paper is based on a case study of a transgender therapy group I facilitated in Oslo in January and February 2013. The two interlinked research questions are: How can a Gestalt therapist approach gender identity issues and transgender people in particular? What are the important experiences and changes that transgender people report from a Gestalt-inspired group? The case study particularly highlights the importance of phenomenology, polarities, and certain modes of contact, and it illustrates the practice of the former in three case descriptions and discussions. The paper concludes that Gestalt can work as a transpositive approach in accordance with a new paradigm within transgender health, the “Transgender Model.” In addition to working with transgender clients, Gestalt therapists should also address gender identity issues within the larger social field, including norms and polarities on group and societal levels.