Current literature shows that parents of trans and gender-diverse children relearn gender from their children to fulfill their parenting role. In-depth interviews with 35 mothers raising teens in a progressive region of the United States reveal that mothers of cisgender children must also relearn gender to parent successfully, and they utilize their children’s generational gender literacy to do so. Using the theory of gender as structure, I argue that, in a progressive community, transitions on the institutional and individual levels of gender created a shift on the interactional level, causing mothers who were socialized into gender as binary and stable to reconceptualize it as fluid and to adopt appropriate gendering conduct. In the new generational and local regime, accountability, thus far conceptualized in gender theory as reinforcing heteronormativity, became a tool for enforcing conscious gendering conduct. Furthermore, despite theories of gender and sexual socialization flowing from parent to child, I find that children had access to individual and institutional-level resources helping them adapt to the new gender regime. Children thus became tutors and cultural resources for their mothers, illustrating that the direction of gender socialization may depend on cultural fluency rather than family role.