The definition of distance education (DE) is established with propositions and constructs, for example, the theory of transactional distance education. Transactional distance theory is conceptually critical to distance education for it proposes that the distance in distance education is transactional and not spiral or temporal. It is this transactional nature of DE that demands a transition through the curriculum delivery grid, through various pedagogical implications, from fully offline to fully online. The theory of the transactional DE connotes the interplay between the environment, individuals, and the context in an educational setting. The purpose of this work is to identify difficulties experienced in transitioning through a curriculum delivery grid for industrial engineering students at Unisa. An investigation based on a qualitative research approach that includes the epistemological beliefs emanating from the case study research method is adopted. The findings of this research will present the types of barriers encountered, their characteristics, and the source of these barriers. The impact of the barriers experienced by the students and instructors alike will be discussed and deliberated further. In addition, the research will be complemented with a recommendation of a remedy to the barriers experienced by the participants in the educational setting.