Japan is famous for technological advancement, spanning from high-speed trains, the automobile industry, and medical equipment to portable gaming and music devices. With this wealth of sophisticated technology at its disposal, people outside of Japan often may assume that this technological prowess is also well integrated into every phase of Japanese people's lives, including the education system. In point of fact, however, the integration of technologies in Japanese education, particularly within the higher education segment, is far behind that of other highly developed countries. Japanese online education has therefore also been lagging due to the low adoption of technologies in Japanese higher education settings and various cultural challenges surrounding education and employment present in the country. This article presents a basic overview of the Japanese educational system, highlights two Japanese institutions that have "found their niche" within online and distance education and promising future outlooks for high-quality online education, and concludes with a brief examination of the pedagogical and cultural shifts and collaboration between government, industry, and higher education, which are all essential to make online education a viable option for Japan's future.