The chapter presents challenges which limit the preparation of students with disabilities for learning in higher education, in rural schooling in the South African context. A lot of research has revealed that while there has been increased access into higher education by learners with disabilities, there is a gap in which students with disabilities fail to cope in terms of learning and consequently do not succeed. However, little is known about the challenges confronted in the preparation of learners with disabilities to be able to learn in higher education, in rural schooling in the context of Africa broadly, and in the South African context specifically. Data were collected through scanning South African literature on low resourced rural contexts of schooling. Selected texts were synthesised and analysed, using specific theoretical concepts from Critical Disability Theory. The findings revealed that rural schooling in South Africa is still limited in terms of preparing learners with disabilities to cope in learning in higher education. There are complex contextual factors resulting from social and economic disadvantages such as extreme poverty, perpetual poor service delivery, lack of resources and materials, poor infrastructure, large classes, mental health issues, poor nutrition, and unemployment that limit the preparation for all disadvantaged students. However, there are specific challenges that have an impact on learners with disabilities. These are lack of training on inclusive education on the part of teachers, lack of knowledge on disability, out of school experiences, and cultural beliefs on disability, which result in exclusion, hence lack of preparedness to learn in higher education by learners with disabilities. The argument for the chapter is that learners with disabilities have the same potential to cope in learning in higher education and succeed as students without disabilities if there could be adequate preparation in terms of learning to learn from schooling. It is hoped that the chapter will contribute to the complex debate of understanding rurality as well as specific challenges for learners with disabilities in the context of rural schooling in Africa broadly, and the South African experience specifically.