As U.S. elite independent schools become more racially inclusive, white students may perceive a shift in their social position. Using qualitative data from school climate surveys at 10 such schools, 2014-2018, we explore how white adolescent boys experience these shifts emotionally. We find that a subset of particularly vocal white boys express key characteristics of white fragility and colorblind racism both in the negative feelings they report and the frames they use to explain race relations in their social worlds. Other boys, in contrast, show signs of a developing critical consciousness around race and racism in school. The findings underscore adolescence as a critical period for intervention on the developing perspectives and emotions of white boys. We conclude with a discussion of the necessity of a closer examination of how independent schools reckon with structures of whiteness in their culture as they attempt to engage in diversity and equity efforts.