This chapter is an empirical qualitative research study conducted with the administration, teachers, and students at a private K-8 school for students with diagnosed learning disabilities in the mid-Atlantic region after they experienced intensive professional development on critical race media literacy (CRML) and associated topics across the course of many months. This chapter begins with a rich description of the school and the problem that the adults in the school started to notice following a pivotal national tragedy leading to the death of a young Black man. Teachers and administration wanted to lean into their foundational mission to bring about new and deepened awareness among their students of race, racism, and empathy. Up to this point in time, the school’s pedagogical mastery leaned heavily on providing students with learning disabilities skills to better manage the literacy domain. This chapter describes the ways that the administration realized that they could go beyond this and make a shift toward criticality using media literacy as it was delivered by one of the authors and experienced by the other, a teacher at the school. Beyond the rationale, the participants describe the ways they and/or the school has grown, as a result of CRML.