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Using critical whiteness studies as a frame, we describe an online book study project developed with preservice teachers around Debby Irving’s (2014) Waking Up White and Finding Myself in the Story of Race. We focus our analysis of two participants, Haley and Brooke [pseudonyms], whose contributions reveal contrasting responses to several of Irving’s more prominent themes; specifically, (1) understanding racism as related to self; (2) grappling with white dominance; (3) and reflecting on white identity. We situate our analysis within the critical whiteness studies literature. We discuss some of the challenges of doing antiracism work with preservice teachers and consider how we can leverage what we learned from Haley and Brooke in designing future pedagogy.