Accompanying myriad definitions of critical literacy is an absence of pedagogical models for implementing critical literacy in teacher education contexts. This action research explores critical literacy with pre-service and in-service teachers in teacher education courses offered in the United States. The primary data sources include online weekly discussions on course readings in the TESOL methods courses I taught in Hawaii and Kansas. First, I propose the working definition of critical literacy in the study (Luke, 2012) and then present course participants’ perceived challenges of employing critical literacy in their current and future classrooms. Findings reveal that despite the differences in the two instructional contexts, both groups recognized that the current standards-based, test-driven educational environment would be the major obstacle for enacting critical literacy in their classroom. In addition, the lack of understanding of critical literacy was addressed by both groups of teachers. I also discuss my struggle and dilemma as a critical teacher educator. Finally, this article concludes with suggestions for introducing critical literacy in teacher education contexts.