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The World Wide Web is playing a vital role in today's digital world. Most enterprises are becoming digital. Also, students and regular web users are turning their personal Web sites into small digital enterprises. Therefore, it is necessary to make the process of developing digital enterprises as automated as possible. A feasible way to build a digital enterprise is to use an appropriate content management system, which automates most of the application requirements. A few case studies are reported in this paper to explain how the rapid prototyping process can be made easier using content management systems. These case studies include rebuilding an existing Web site (ETD) by enhancing its features and building a prototype for a proposed Web site (SEBE and SDPS).