We defined diagrams called Web transition diagrams to represent overall behavior of Web applications. Using these diagrams, we can generate server program type Web applications such as CGI-based Web applications, and server page type Web applications such as ASP-based Web applications. The purpose of this paper is to design Web transition diagrams to represent wider class of Web applications based on JavaServer Pages (JSP)/Servlet architecture. Then we present an automatic generation method of JSP/Servlet Web applications from these diagrams. We implement a software system called T-Web system which enables Web application designers to visually compose Web transition diagrams and generate Web applications from these diagrams without any manual programming. T-Web system can generate both H™L-based Web pages and XML-based Web pages for Web applications. Generated Web applications support standard level of security against attacks, the use of HTTP cookies, user authentication, and session management.