Previous studies of communities of practice had often emphasized the ease with which members are able to participate in the collective learning process through joint practices within a particular community. However, nothing much has been done to reveal the difficulties and problems of learning between different communities due to different and sometimes conflicting identities and power inequalities. This article reports a failed experience of a tertiary institution to outsource its information technology (IT) department. By highlighting the social conflicts experienced by the in-house IT technicians in coordinating with the outsourcing staff, we argue that the received unitary, managerialist viewpoints of communities of practice somehow neglect the broader social context and micro-political factors of learning. This neglect underestimates the critical challenges of resolving the social tensions caused by multiple identities and embedded power differentials across different communities of practice.