This paper aims to share the outcomes of a qualitative survey on the status of elearning implementation in Japanese higher education institutions. The research evidence is gathered through: 1). a literature survey related to e-learning in Japan, 2). analysis of the websites of the universities, 3). observations obtained during Tokyo e-Learning World 2005 Expo and Conference, and 4). interviews conducted with the faculty members at the working on e-learning projects in the universities visited. The survey revealed that e-learning has not been adopted by Japanese universities wholeheartedly despite the availability of a highly developed ICT infrastructure nationwide. The main reasons for such gap between technological availability and its actual implementation can be attributable to the lack of support systems to facilitate the utilization of ICT in instructional processes and the lack of long term strategic visions to utilize ICT to enhance teaching and learning in many higher education institutions in Japan. These dilemmas are evaluated from the cultural, societal and managerial perspectives. Cultural perspectives included shared values and customs among policy makers and practitioners. Societal considerations involve the university system itself, its funding structure, and the demand of e-learning among potential students. From the managerial point of view issues such as leadership of university governance and long-term strategic visions of the institution are examined. Finally future prospects of e-learning in Japan are discussed.