In a typical South African contact university, where learning and instruction is done following a strict class schedule, the challenge of providing personalized learning support is still prevalent. This paper argues that the advent of Web 2.0 affords varied opportunities to cushion this challenge, faced by learners. In this paper, social presence theory acts as a lens to provide an informed understanding of the interactions provided by the varied Web 2.0 applications. Empirical evidence was gathered at Tshwane University of Technology through contextual inquiry research methodology. The evidence suggests that the varied Web 2.0 applications have the potential to alleviate the preceding challenge by creating a personalized learning environment where learners may interact, share knowledge and collaborate with those who are not in the same location. This, in turn, strengthens the learners’ skills as they interact with knowledgeable peers and instructors. The paper concludes that utilizing Web 2.0 appropriately may alleviate the challenge of providing personalized learning support, faced by South African higher education.