The abstract value of academic freedom is enjoyed (or not) in concrete settings, as interactional and emergent experiences. We examine classroom political controversy in our experiences, understandings, and values, using grounded theory methods and collective autoethnography by a team of five teachers and students. Our data were generated through electronic and face-to-face dialogues. Our analysis, guided by a symbolic interactionist and constructionist framework, yields a picture of Controversy in Action, whereby we navigate Barriers to Open Discussion and Costs of Controversy. Results highlight insights into taken-for-granted meanings unexamined in day-to-day classroom interaction. We attend to the relevance of the local context in which our classrooms are embedded and the interactional, meaning creating work that goes on in those classrooms, as we negotiate controversy.