A central issue in the practice of organizational learning concerns the relation between knowledge of individuals and knowledge on the level of an organization (Cohen, 1991; Cook & Yanow, 1993; Weick & Westley, 1996). The cultivation of various communities—formal or informal—throughout an organization, seems to fill an intermediate level of learning between the organization as a whole and individual organizational members (Wenger, McDermott, & Snyder, 2002). There, knowledge links among individuals are established and communal organizational knowledge is collectively contributed and made available to the rest of the organization. In their study of “communities of practice,” Brown and Duguid (1996, p. 60) described learning as a bridge between working and innovation through their activity theory of knowledge, which could be explained by the notion of exploitation and exploration (Cohen & Bacdayan, 1996; Holland, 1975; March, 1991). Exploitation entails the efficient use of existing competencies in terms of decontextualized, codified, and formalized rules of operation. Inevitably, such rules cannot cover the richness and the variability of practical contexts. It is by context-dependent changes from the existing rules (exploration), with the ensuing need for improvisation and experimentation that learning arises, in interaction between members of the community. Oftentimes, exploration is based on storytelling, to capture and share context-bound experience, and to guide experimentation. In the process of learning, exploitation is based on exploration, and vice versa: we exploit what we have explored, and it is on the basis of exploitation that we explore. The extent to which exploitation and exploration can be combined in time and place depends on our ideas of community development, especially for online communities in today’s Internet age, and the deliberation of information technology through the design of suitable information systems (IS) support. To pursue the goal of organizational knowledge synthesis, there is a strong need to leverage the knowledge embedded in the people of the organization. This need of knowledge sharing among potential communities within and beyond the organization has been well exemplified in the notion of a learning organization (LO) (Garvin, 1993; King, 1996; Levine, 2001; Senge, 1990), which could be considered as an organization, which helps transfer learning from individuals to a group (and vice versa), provide for organizational renewal, keep an open attitude to the outside world, and support a commitment to knowledge. The theme of this article is, then, to examine the knowledge processes required of the learning organization viewed from the online communities’ standpoint, to develop and sustain the communal knowledge base (Davenport & Prusak, 1998; Hackbarth & Groven, 1999; King, 1999; Levine, 2001; O’Leary, 1998) through the elaboration of appropriate IS (or LOIS) (Williamson & Lliopoulos, 2001) support so as to expand an organization’s capacity to adapt to future challenges.