Practice, that is, the execution of work relevant tasks, can take two forms: actual and espoused practice (Brown & Duguid, 1991). Espoused practice is formally and deliberately planned: formal organizational structuring, product manuals, error detection, and correction procedures represent just a few examples. Actual practice represents the solutions to problems and the execution of tasks as they really happened in a given context. Processes of knowledge generation and transfer are different for espoused or actual practice (Orr, 1996). While traditional modes of organizing work practice focus on espoused practice, newer organizational forms focus on actual practice: Communities of practice are groups of people bound together by shared expertise and passion for a joint enterprise on behalf of an organization (Wenger, 1998). To support effective work practices in an ever more distributed work environments, collocated CoPs are complemented by virtual communities of practice (VCoPs). Its members interact supported by collaborative technologies in order to bridge time and/or geographical distances. Toolkits of computer-mediated environments facilitate community building in addition to personal interaction (Hinds & Kiesler, 2002; Walther, 1995; Wellman et al., 1996). There is a shared understanding that VCoPs are an especially effective organizational form for knowledge creation both within companies (Kogut & Metiu, 2001; Nahapiet & Ghoshal, 1998; von Krogh, Spaeth & Lakhani, 2003) and between companies (Constant, 1987; Vincenti, 1990). Therefore, VCoPs are managerially desirable forms of virtual communities (Rheingold, 1993; Smith & Kollock, 1999; Wellman et al., 1996) in which learning in practice takes place; that is, professionals stick together because of exposure to common problems in the execution of real work. The “glue” which binds them together is a powerful mixture of shared expertise and experience, as well as the need to know what each other knows. Given that VCoPs offer such potential to enhance intellectual capital and to enrich social processes within companies, we look more closely at the social and knowledge generation processes within VCoPs from a managerial point of view. Viewed from this angle, VCoPs represent a difficult challenge for managers who want to profit from using them as an arena for desirable learning in practice. Although VCoPs are believed to be a desirable organizational form for knowledge generation, they are preferably modeled as a rather emergent phenomenon and believed to be only marginally manageable. Thus, on one hand, managers are urged to believe that VCoPs are something beneficial while, at the same time, they are told that VCoPs cannot be managed deliberately.