This article investigates one undergraduate's path towards critical literacy around racial inequalities as a result of engaging with, reading, and discussing a challenging children's novel during a book study with peers. Using Cultural Historical Activity Theory, the author examines the personal and cultural resources the students brought to the experience, the stances she developed while engaging in the book, and the contextual resources that mediated her understanding of racial inequalities. This article further investigates how educators can leverage challenging texts in classrooms to support critical literacy development around societal issues.