This is a multiple case study exploring five high school English teachers' perceived supports and challenges to enacting critical literacy pedagogy, and their experiences navigating the challenges. Through a structure/culture/agency framework, I sought to understand how these five teachers' leveraging of supports and sense of agency in the face of challenges impacted the critical literacy choices they made in their classrooms. In order to understand how participants' pedagogical challenges, supports, and agency all intersected to impact their critical literacy teaching, I used critical narrative analysis to explore the presence and/or absence of grammatical and framing agency in their narratives. The analysis found that participants mostly experienced challenges at the local (school) and institution level contexts, and navigated these challenges differently depending on the level of agency they saw themselves having in their schools.