The growth of middle-class families in gentrifying neighborhoods has sparked questions about how these families select schools for their children. Research on elementary school selection has found that some parent gentrifiers are willing to try their neighborhood public schools. These parents are often motivated by civically oriented values, including supporting public education and supporting neighborhood schools. The field knows much less about parent gentrifiers' decisions for middle and high school. This study draws on interviews with 20 parent gentrifiers in Washington, DC, to understand how parents choose middle and high schools. This study finds that secondary school selection is a fraught process throughout which parents weigh multiple sets of values, including civically oriented values and specific school attributes from which parents believe their children can derive value. This study's findings underscore the tensions and contradictions of school choice and gentrifying contexts.