The purpose of this qualitative study was to understand the role of dialogic teaching in fostering critical literacy in an urban high school English classroom. The study was framed by sociocultural, dialogism, and critical literacy theories, in which the researcher paid particular attention to the contexts that shaped dialogue before, during, and after critical discussions of literature. The researcher used a Participatory Action Research (PAR) orientation, an ethnographic methodology, and discourse analysis methods to explore a dialogic approach to critical literacy and teacher perspectives on the approach. The findings from this study demonstrate that while a dialogic approach supported critical literacy, certain aspects of critical literacy were difficult to enact. The teacher cultivated a dialogic environment and afforded students with opportunities to have meaningful dialogue toward critical literacy ends, but she also experienced ideological conflicts that often complicated the path toward critical literacy. Implications of the study show the promise of dialogic teaching in valuing culturally-and-linguistically diverse students’ contribution during the meaning-making process. This study underscores the importance of understanding the teacher’s role in shaping the direction of critical dialogue and advocates for educational policies that position teachers as transformative intellectuals in the classroom.