This chapter introduces and investigates the applicability of the multiagent paradigm for engineering and developing CSCW systems with the aim of advocating modern design dimensions and software engineering implications. It argues that the use of multiagent systems can significantly improve and enhance the functionalities of computer supported work systems. To meet such an objective, the chapter raises the importance of “revisiting” the context and domain of CSCW in accordance with the growing organizational transformations, situational shifts, and technological developments. While such changes are motivating group collaboration, the information systems that support them must be powerful. The author believes that because of their specific limitations and the continuous changes in the collaboration environment, there is an urgent importance of using thorough system-oriented approaches to address the way they evolve. Furthermore, the chapter draws a framework for the use of the multiagent paradigm to understand and deploy CSCW systems by adopting an integrated context of analysis that improves our general understanding about their potentials.