In South Africa, higher education is a constitutionally enshrined basic human right and one of the cornerstones for accomplishing the ideals of offenders’ rehabilitation and preparation for life beyond bars. However, acquiring higher education whilst serving a sentence in a correctional centre is compounded by many institutional challenges especially towards incarcerated female students. Framed by the transactional distance theory (TDT), the qualitative study from which this paper emanates, used purposive and snowball sampling to recruit twenty-nine female distance learning students incarcerated at four female correctional centres across three provinces in South Africa. Based on the thematic content analyses of the data, the findings indicate that there is restricted access to learning resources, and that online participation in both learning and assessment is affected by erratic internet connectivity caused by UNISA-DCS hubs (computer laboratories) due to the security-focused nature of the correctional centres. Furthermore, the lack of direct access to the internet, smartphones, or internet‐enabled devices exacerbates the digital marginalisation and exclusion of incarcerated students which engenders feelings of despondency against a system that is meant to empower them. Thus, owing to these findings, the paper recommends that practitioners, researchers, and policymakers must endeavour to design not only inclusive, but correctional centre-friendly student support. This entails acknowledging that incarcerated students do not have 24/7 access to the internet, the technological gadgets that make online learning possible and some incarcerated students having limited digital literacy. There is a need to design learning policies and strategies that are flexible to enhance the learning experiences and graduateness of incarcerated students.