This paper critically examines some of the challenges that white educators who interrogate whiteness with white students encounter. Two specific dilemmas are addressed: Is one supporting white students' learning when one tries to teach from the place "where the student is" and/or is one colluding with whiteness by appeasing white discomfort and protecting white fragility, one's students as well as one's own? Does one interpret what white students say as a query to be responded to or as a white distancing strategy that requires disruption? Each pedagogical challenge is described and debates around these issues are explored. Emphasis is given to the effects on students of color when white educators fail to respond appropriately. Implications for white progressive educators are drawn out. Two recommendations are discussed: Being willing to rock the boat and cultivating white double consciousness.