In March 2021, Hannah Wallerstein and Jordan Osserman facilitated a live dialogue over Zoom on the subject of transgender young people, with four psychoanalytic clinicians and thinkers. The conversation draws on short essays submitted in this section of The Psychoanalytic Study of the Child as a springboard for discussion. It has been transcribed and edited for length and clarity, and is reproduced here. Questions explored include the differences surrounding gender identity in childhood versus adulthood, the use of medical interventions for children experiencing gender dysphoria, the tension between psychoanalytic neutrality and affirmation, and the ethical stakes of working in this field.