This paper examines how educators in the U.S. public education system speak to their colleagues about racially oppressive beliefs and practices. Limited research exists that examines the experiences of educators who exercise voice to challenge and engage co-workers and supervisors around issues of racism in their schools. Using data from semi-structured interviews with 25 educators and a flexible coding approach, the authors found that participants described using cautious, covert, and indirect approaches with their White colleagues to increase the likelihood that their messages would be received and to decrease the personal and professional consequences they might face for openly challenging their colleagues' racist beliefs or actions. This cautious approach serves to reinforce the dominance of Whiteness and White fragility in the context of anti-oppressive practice. Examples of an alternative to a cautious approach are presented and recommendations are made for future research and teacher education.