We look at the difficulties and benefits of the implementation of newest technology in Thailand by the method of leapfrogging. In the investigation we find that a variety of issues influence the uptake of a new technology; namely the extent of the cultural shift, Government support and initiatives and the take up of these initiatives by the education and private sector in terms of R&D and training. We also examine and define areas fundamental to the preparedness of a nation for the introduction of electronic commerce; that is, telecommunications, Internet penetration & development, and technology Parks. We conclude with a recommendation to initiate a study of Information Technology education take-up in universities to support technology leapfrogging initiatives implemented by the Thai Government, identifying a number of questions that need to be addressed. Further, a strategy to encourage small communities and businesses through community education programs is suggested, including a pilot project recommendation to test the successful implementation of this strategy in a community in Chiang Mai Thailand, that would also document the issues identified, including Government and cultural impacts, in order to establish a model that could be replicated and implemented in communities at large throughout developing countries.