This study investigated how teenagers reacted to parental regulation of technology. Using longitudinal dyadic interviews with 24 teenagers and their 21 parents in two predominantly white middle-class communities, we explored how teenagers used technology during the COVID-19 pandemic and the differential consequences parental interventions had for teens’ well-being and confidence with technology. Parents’ narratives and actions about technology use were deeply gendered. Boys felt confident about their self-regulation of technology, and parents did not substantially limit boys’ technology use during the pandemic. Girls were less confident about their ability to self-regulate and either worked with their mothers to manage technology, distrusted parents who monitored them, or lacked access to virtual hangout spaces such as video games and social media. The findings illustrate how parent-teen dynamics around adolescent technology use can produce short-term gendered inequalities in teenagers’ well-being and result in long-term disadvantages for girls.