Across the country, effort is underway to restrict discussion, learning, and student support related to race and gender/sexual identity in educational settings, targeting schools with state legislation and politicians’ orders; national conservative media and organizations; Board directives; and local actors wielding media-fueled talking points. To date, few analysts have yet explored in detail educators’ lived experiences of these multi-level restriction efforts and local responses to them. In this article, we analyze 16 educators’ experiences of 2021-22 restriction effort and local responses, with an eye to potential effects on student support and learning. Educators interviewed emphasized their recent experiences with talking about race and LGBTQ lives, with many emphasizing threatened punishment by critics for discussing these topics. Context mattered tremendously: While some educators enjoyed support and freedom in race and diversity-related discussion and learning, other educators described intensive restriction effort emanating from local, state, and national pressures. Respondents also indicated that responses from local district leaders, school leaders, and other community members amidst such multi-level restriction efforts were crucial in effecting restriction or protecting the ability to talk and learn. Data from this interview study suggest that the nation may be heading toward two schooling systems: one where children and adults get to talk openly about their diverse society and selves, and one where they are restricted or even prohibited from doing so. The fate of our nation’s teaching, learning, and student support is up not only to the nation’s teachers, principals, and superintendents, but us all.