Since the onset of COVID-19, social protest has expanded significantly. Little, however, has been written on prison-led and prison justice organizing in the wake of the pandemic—particularly in the Canadian context. This article is a case study of prisoner organizing in Canada throughout the first 18 months of COVID-19, which draws on qualitative interviews, media, and documentary analysis. We argue that the pandemic generated conditions under which the grievances raised by prisoners, and the strategies through which they were articulated, made possible a discursive bridge to the anxieties and grievances experienced by those in the community, thinning the walls of state-imposed societal exclusion. We demonstrate that prisons are sites of fierce contestation and are deeply embedded in, rather than separate from, our society. An important lesson learned from this case study is the need for prison organizing campaigns to strategically embrace multi-issue framing and engage in sustained coalition building.