A Web-driven problem-based learning environment and instructional system was conceived and developed to study the marriage of the problem-based learning instructional method and Web technologies for instructional delivery of educational administration content material. The project described herein was undertaken to examine the efficacy of implementing this new mode of instruction in graduate courses in educational leadership. The ultimate goal of this line of research is to enhance the development of applications of Web technologies to support problem-based learning and improve the efficiency and efficacy of this instructional form in practice across higher education settings. This article describes the prototype software, the rationale and theoretical framework supporting its development, the process and results of research conducted during production and beta-testing, and the educational significance of the project.