This mixed-methods study explores the impact of teacher preparation coursework on 141 teacher candidates' understandings about educational equality, school achievement, and meritocracy. Framed by pedagogies of discomfort, the program included readings, discussions, simulations, films, and direct work with emergent bilingual students. Findings from an analysis of surveys, interviews, and class discussions indicate that the program (1) complicated candidates' understandings of school achievement and meritocracy in urban, underserved communities and (2) prompted participants to see students and themselves differently. These findings inform new pathways for enhancing candidates' ability to critically understand school achievement within complex systems of systemic advantage and disadvantage.