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This study builds on scholarship that reveals that teachers perceive myriad dilemmas that prevent the instruction of multicultural young adult literature, a genre that features characters and themes relevant to students today. Two overarching lines of thinking guided the study: Critical Whiteness Studies and Dilemma Management. The study explored the dilemma management strategies of nine White teachers using multicultural young adult texts in urban schools. Findings revealed that teacher participants who were reflective and aware of Whiteness focused intensely on including students in conversations to manage dilemmas. The study is significant in the ways it offers insight that might better prepare teachers to feel confident in their instruction of these texts and discussions of complex issues like race and privilege.