This panel will bring together instructors with diverse experiences teaching history in correctional facilities. Our goal is to examine the varied ways in which we have approached teaching courses on topics ranging from twentieth-century U.S. history to global women’s history. Additionally, this panel will consider the structural differences between teaching history classes in collegiate versus carceral settings, the latter of which are more often than not underfunded, overcrowded, under-resourced, and undergirded by a subtle tension between correctional officers and incarcerated individuals. Teaching history at the collegiate level requires broaching charged topics such as imperialism, racism, and misogyny as well as modeling practical skills including research, writing and editing. As instructors in carceral settings, our ability to navigate complex topics while at the same time instilling a knowledge of historical practice can be limited by censorship processes or sometimes challenged by a lack of resources. Given the increasing number of higher education programs in correctional facilities across the country (40 new programs were founded in the year 2020 alone thanks to funding from the Second Chance Pell Experimental Site Program), a likewise increasing number of instructors and incarcerated students have much to gain from the prioritization of dialogue between instructors across programs.