Imprisonment pains often accompany confinement to correctional institutions. Less is known about how related discomforts and deprivations might specifically impact the administration and receipt of postsecondary correctional education. This paper will show how encounters between incarcerated college students, other prisoners, prison educators and corrections officers can influence higher learning in correctional settings. It is based on a qualitative study and inductive analysis of data collected from interviews with 34 formerly incarcerated individuals who were also past and present members of a higher education program in the United States post-release. This research has important policy implications given that incarcerated persons who engage in productive activities such as higher education are better positioned to cope with carceral strains in legitimate ways. It can also help educators and correctional staff develop programs that account for the specific educational challenges of the prison sub-culture.