The premise for this chapter is that learning and knowledge sharing is a human-to-human process that happen independent of space and time. One of the essential facets of learning is the social interaction in which personalized knowledge support is an outcome of learners sharing experiences. To this point, this chapter does not directly address a specific learning management system (LMS) platform but addresses forms of communication that can be encountered as tools of LMS platforms. The chapter argues that LMS ought to be able to facilitate the social interaction among learners not confined to particular places. Learners, because of their mobility, perform tasks in three varied locations or contexts: formal contexts, semi-formal contexts, and informal contexts. In this chapter, learners use social awareness to determine the appropriateness of an LMS tool to engage in a knowledge activity, as they traverse the varied contexts. Thus, the chapter posits that a ubiquitous personalized support and on-demand sharing of knowledge could be realized if a learning management system is designed and adopted cognizant of learners’ social awareness.