The power of Internet provides unprecedented opportunities for learners to obtain diverse content and for educators to quickly distribute resources. In the increasing globalized learning environment, OpenCourseWare (OCW) is one of the recent movements to utilize the Internet in making educational materials freely available to the world. However, the fact that these materials are offered mainly in English poses challenges to the non-English speaking population in many parts of the world. In response to such concern in the Great China Region, a localization project called the Opensource OpenCourseWare Prototype System (OOPS) was born in Taiwan in February, 2004 (Lin & Chu, 2005). OOPS aims to break the language barrier and deliver the openly-accessible English educational materials to the Chinese-speaking audience in their native language. This chapter presents the detailed background and history of this project, and highlights three challenges that OOPS has faced in its early stage of development. They are: (1) access to materials, (2) issues about translation, and (3) complexity of intra-cultural communication. Based on the first author’s direct experience with the project, suggestions and implications for future research are also offered.