The articles and essays in this volume continue the efforts of the inaugural volume of the Journal of Higher Education in Prison (JHEP): to create space for an emerging intellectual community and to publish work that is representative of the challenges and limitations of teaching and learning within prisons. The Call for Submissions for Volume Two of JHEP was publicized in March 2021, and the second volume is publishing three types of essays: Contemporary Perspectives, Keynote Address (from the National Conference on Higher Education in Prison), and Articles.