Since the late 1990s technology has become a central component of national education policies in many Asian countries. In Singapore schools, for instance, technology has become central in teaching, learning and administration. On the other hand, Japanese schooling has been largely impervious to advances in educational technology. This paper aims to stimulate discourse between policy makers, teachers, researchers and the community in Japan and internationally to consider informed, meaningful strategies required for developing suitably skilled pupils for today's Digital Age. The paper begins with a summary of Singapore's technology centric education policy, called the "Masterplan for IT in Education". The Japanese context is then summarised and a number of recently proposed educational reforms are discussed. It will be argued that these reforms do not lend themselves to supporting the necessary development of digital competency required of Japanese school pupils in the 21st century. To overcome the shortcomings, strategic actions to support meaningful ICT integration in education, influenced by the Singapore experience, will be proposed. (Contains 6 tables and 1 figure.)