The roots of American sociology of race and ethnicity run deep, but a focus on whiteness has matured in recent decades. This body of research is diverse: Whiteness is understood as simultaneously omnipresent, ubiquitous, rigid and flexible. Moreover, students enrolled in courses on race and ethnicity have difficulty grasping the conflicting and ambiguous character of whiteness that is exacerbated by their own misconceptions and ideological baggage they carry into the classroom. To empirically identify common student misconceptions, and to illuminate effective pedagogical interventions, I analyze two different sociology of race and ethnicity courses, offered twelve times over an eight-year span, at two different University institutions. Based on in- and out-of-classroom exercises and assignments completed by students in these classes (N = 406), I outline four patterned interpretative dilemmas and concomitant pedagogical interventions to aid students’ understanding of whiteness. Results indicate that these four intervention exercises found overall success amidst a variety of classroom sizes, disparately ranked public universities, different US regions, and amongst classroom contexts high in racial diversity to majority-white student course enrollment