Critical social analysis is a foundational sociopolitical learning experience which supports youth development and social action. While practical guidance for facilitating critical social analysis exists, there is a need for empirical work exploring educator and participant experiences. To understand how urban educators implement critical social analysis and how participants experience it, reflective interviews were conducted with adult leaders and former youth organizers in Teen Advocates for Sexual Health. In a highly-segregated midwestern city, leaders engaged diverse youth in critical social analysis and social action around access to comprehensive school-based sexual health education. Three empowering interpersonal processes supported critical conversations on power, privilege, and sexual health. First, adult leaders established norms for power sharing and group communication. Second, leaders helped youth distinguish between feeling uncomfortable, integral to social justice learning, and feeling emotionally unsafe. Third, leaders supported emotional safety, allowing youth to determine their level of participation. Youth were empowered to remain engaged when uncomfortable, take action if they felt unsafe, and share responsibility for community safety. Combined with other organizing experiences, critical social analysis empowered participants as teens and contributed to adult social justice commitments. Findings contribute to literature on how urban educators can support sociopolitical development across settings.