Abstract: Contested white students often feel caught between two worlds, liminally situated, betwixt and between monoracial constructions of race. They are a subset of undergraduate and graduate students who are differentially located along the borders of whiteness, but who share common experiences of racial ambiguity, insecurity, and contestation. Contested whites report being under constant pressure to explain and justify their racial location along the borders of whiteness. Their narratives of racialization powerfully reveal the operations of whiteness-at-work in fleeting, everyday moments in U.S. universities and colleges. This manuscript tells the stories of Fly on the Wall moments for three contested white graduate students. I use critical discourse analysis and critical narrative analysis to explore how Fly on the Wall moments reveal iterative, paradoxical constructions of whiteness-at-work. Implications for postsecondary education are explored.