Utilizing a critical whiteness studies framework, the authors analyzed the experiences of a cohort of predominantly White pre-service social studies teachers discussing race and Whiteness in relation to education. The pre-service teachers resisted identifying White privilege as a form of structural racism, instead preferring individualized understandings of racism. The participants also utilized their personal biographies to accept or reject aspects of race privilege. The authors highlighted three tensions for teacher educators to consider when engaging pre-service teachers in discussions about race privilege, including recognizing the unfamiliar nature of structural thinking, appreciating the limitations of personal experience, and acknowledging the challenges of structural considerations within individual classrooms. The authors' findings--and the tensions they highlight--depart from previous literature on White teachers and race by paying specific attention to pedagogical issues related to developing a critical racial consciousness in White teachers and by attending to the ways in which Whiteness, as a structural force, limits the ability of White teachers to engage in conversations about race. The authors attempt to trouble the assumption that the pedagogical practices in teacher education adequately create an environment in which White teachers can thoroughly engage in the problematics of race, racism, and Whiteness.