How do emerging and enduring conditions of motherhood in Taiwan shape mothers’ interactions with children who are gender or sexually nonconforming? Bridging research on the transformation of mothering discourses in Taiwan and globally with the small but growing body of work on LGBT family of origin relationships, this article argues that women’s experiences of raising gender and sexually nonconforming children are integrally shaped by the conditions of gender and family inequality in their own lives. These inequalities are sometimes challenged but often reinscribed by new parenting discourses and resources that have proliferated in late 20th and early 21st century Taiwan, including new forms of parental labor, accountability for child outcomes, and emerging expert voices on sexuality and parenthood. This analysis is rooted in ethnographic fieldwork and family history interviews with gender and sexually nonconforming people and with their families of origin throughout Taiwan, with emphasis on heterosexual mothers’ narratives.