When a child resists gender socialization, many parents struggle to understand the path forward. Even supportive parents trying to help a gender-nonconforming child navigate a gendered world experience stress. These stressors are extended to the family. Through their attempts to navigate support for their gender-nonconforming children, parents are often without support or assistance when faced with systems of institutional power such as education, medicine, and government. This case study examines the complexities of being a supportive parent of a trans-identified child and the emotional, physical, and financial stress on the parent/family, using a feminist ethnographic approach. This case study of Jen[1], a mother of four children including Evan who is a 15-year-old trans boy, attempts to offer the important perspective to educators, administrators, and health care providers. Through reading Jen’s narrative, power brokers and gatekeepers within the medical and educational systems (teachers, administrators, doctors, and other health care providers) can gain some empathetic insight to assist parents.