We report on lessons learned in the first two years of the pandemic that were gleaned from a unique partnership with three carceral systems and based on 100 interviews we conducted with incarcerated people, correctional workers, and medical staff. They point to unique structural and operational challenges that carceral facilities face in prioritizing the goal of COVID-19 mitigation and highlight strategies that may improve pandemic preparedness. From this work, five dominant themes emerged that provide an “on-the-ground” perspective of living through COVID-19 in carceral settings and center the voices of those incarcerated and working in carceral spaces to capture the complexity of COVID-19 prevention and mitigation.