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In a contact university, learners from diverse backgrounds face different challenges including the provision of personalized learning support. Most of these learners come from previously disadvantaged schooling systems where contact or one-on-one interaction with an instructor is unusual due to the poor faculty-to-learner ratio and scarce resources. With the existence of Web 2.0, there are opportunities to cushion those challenges faced by learners, by incorporating a personal learning environment. Using theories of social presence and connectedness as lenses, this paper, provides an informed understanding of the interactions (whose outcome is learning) provided by varied Web 2.0 tools. Supporting empirical evidence gathered at Tshwane University of Technology through a Contextual inquiry research methodology, this paper shows how Web 2.0 tools facilitate personalized interaction between learners, as well as personalized interaction between learners and instructors, to provide ubiquitous access to social resources and other learning resources. The evidence shows that different tools available in Web 2.0 creates a personalized learning environment for learners to interact, share knowledge and collaborate with those who are not in the same location. The use of Web 2.0 tools creates a culture of mutual support and collaboration among learners, which in turn strengthens the learner’s skills in interacting with the instructors, tutors and peers. This paper reports on the feasibility and utilization of Web 2.0 as a personal learning environment (PLE). The paper addresses how learners control their learning pace and spaces by engaging Web 2.0 tools. In this paper, we argue that utilization of theses Web based tools affords learners the necessary personalized support, in varied learning contexts.