ABSTRACT Transgender individuals are at risk for discrimination, which can lead to poor mental health outcomes. Social workers are often the health professionals to provide assistance during periods of transition. Social work education programs use simulation-based learning experiences to train students to think independently and respond empathically to clients. Nineteen undergraduate social work students participated in a dyadic simulation with transgender individuals and their cisgender parents, and they received lower performance scores compared to a similar group of students engaged in a simulation with bisexual child and parent dyads. This paper presents research findings and makes recommendations for simulation preparation activities to better prepare novice social workers for direct practice with transgender children and their parents. We conducted this simulation study at a private university in the United States of America.