This chapter explores the potential for the application of agent technology to evolve an information system. In particular, the use of agents to evolve an educational subject management application is viewed in relation to an on-going project. Such software forms part of a courseware information system currently in use, and being further developed at Victoria University. Agent software is an emerging technology that has its roots in artificial intelligence research. With the recent proliferation of “agent” applications in areas such as e-commerce and Internet marketing, many agent applications fall squarely in the domain of Information Systems. Although there is little consensus at present regarding the nature and capabilities of software agents, agent technology may have the potential to advance Web-based subject management courseware to a further evolutionary stage.