The chapter focuses on a study that was conducted in the Eastern Cape’s Mthatha Management Area within a correctional service setting in South Africa. The chapter addresses challenges such as high dropout rates amongst offender learners, low engagement in education and training programs, and diminished motivation amongst prison educators. Utilizing a qualitative research approach and drawing on the behaviorist theory, the study involved six correctional service educators, eight learners, six security officials, and four managers from four centers. Findings highlighted an unfavorable teaching and learning environment marked by lack of classrooms, shortage of educators, insufficient training, and limited support from management. Furthermore, the government has not rectified the imbalances of the past by rebuilding prisons to accommodate rehabilitative needs and has increased the challenges experienced by prison educators. It was also found that the perception of unprofessional correctional services staff toward offenders’ education was cited as one of the main contributors toward a negative educational environment. The study recommends the need for improved educational conditions, recognition of offenders’ education as a human right, and increased recruitment and training of educators to enhance rehabilitation efforts and reduce recidivism.