This article investigates whether parents in the United States and Canada send their children to schools that are similar to the schools they attended. Intergenerational continuity in the type of high school attended may be generated by social status or religious socialization concerns, or simply through familiarity, identity, and network ties built through parents' high school experiences. Social reproduction as well as social identity processes, we argue, explain intergenerational continuity in schooling choices for children. Findings reveal that public schools are the most likely destination for children regardless of the type of school a parent attended. We also find intergenerational continuity in school sector among parents who opt out of traditional public schools. The school sector boundaries vary by educational context, however, with much higher boundaries between most sectors in the United States than in Canada. A notable exception is the very high levels of intergenerational continuity in the public Catholic sector in Canada, which reflects social identities built within the historical nexus of family, community, and religion. We conclude by discussing implications for researchers who study sector effects and school choice as well as practitioners vying for students in an increasingly competitive educational market.