As online technologies and information resources rise in salience, experience has shown (Vat, 2000, 2001, 2002a, 2002b) that online education must be based on theories of learning and instructional design principles to guide usage of the tools and resources for mediating collaboration and social exchanges within communities of learners (CoL). Relatively recent discussions in the literature (Cobb & Yackel, 1996; Marshall, 1996; O’Connor, 1998; Vygotsky, 1978) suggest that learning is increasingly viewed as a constructive process occurring during one’s participation in and contribution to the practices of the community. This is supported by a current shift (Brown et al., 1993) from the cognitive focus on knowledge structures presumed in the mind of the individual learner, to a constructivist focus on the learner as an active participant in a social context. Indeed, we have been witnessing classroom culture being enriched with tools such as the Web-based search engines that mediate knowledge building and social exchanges among peers as participants in discourse communities (Bonk, Medury, & Reynolds, 1994; Bonk & Reynolds, 1997; Fabos & Young, 1999). These communities open opportunities for learners to interact with multiple perspectives, which challenge their existing knowledge constructions and impose cognitive conflicts (Piaget, 1952) requiring negotiations. The theme of this article is to investigate strategies to enhance learning and knowledge sharing in the learners’ communities through the idea of a learning organization model. Its aim is to develop the collective intellect of the CoL through appropriate design of information system (IS) support so as to expand its capacity to adapt to future challenges.