Despite the rapid advancement of technology in the last few decades, accurate, on-time and on-budget completion of information systems development projects is still a vision rather than a reality. The software crisis is still very much alive in the new millennium as it was in the last. The sudden popularity of Internet and electronic commerce poses a new challenge to the software engineering community. With the increasing importance of electronic commerce in the beginning of the new millennium, organizations will be competing to design and develop Web-based applications. However, existing information modeling methods might not be suitable for supporting such activities. This chapter looks at some of the challenges and issues involved in engineering methods for analysis and design of Web-based information systems. It then discusses some of the research directions for information modeling in the new millennium.