In this manuscript, we explore sites of struggle in the inclusion of critical digital literacies (CDL) in teacher preparation programs. Our worked examples explore two authors' teacher-preparation classrooms and the ways in which each attempts to teach about CDL, in the scope of each class, across varying scales. Through a scalar approach, we explore the sites of struggle that each of the instructors face despite the differing contexts within each scale. These sites of struggle include control, bureaucracy, and isolation. In doing so, we aim to shift the narrative around a lack of meaningful, engaging CDL practices in the classroom away from blaming individual educators towards more nuanced understandings of the systemic struggles present within teacher preparation classrooms, programs and educational institutions and structures.