It has been nearly two decades since the education reform movement initiated in Taiwan in 1994. As a consequence of the lift of martial law, this wave of education reform exceeds previous reforms in terms of scale, initiatives, and impacts. Although the performance of Taiwanese students has been in the leading group of various international rankings, the call for an education system that can cater various needs of students rather than focusing on academic achievement has been recurring in the public debate in Taiwan. How to maintain the existing performance and provide opportunities for students with different talents becomes the center of education reform. This paper aims at exploring the path of education reform in Taiwan with a focus on the shifting paradigm of education since 1994. Two aspects including teacher education and curriculum are discussed. We firstly introduce the social context of the recent education reform movement and then explicate the major trends of education reform and various key initiatives. In the third part of this paper, we map out the trajectory of policies, changes, and implementations in the above-mentioned aspects during education reform with the emerging issues, challenges, and future directions. This paper offers international readers insights on how a well-performed education system attempts to improve itself within a complicated and fast-changing social and political context. We argue that unsuccessful reform attempts might provide more lessons than those successful ones. This paper is based on the discussion of two unsuccessful attempts made by the Ministry of Education to reveal the bumping reforming process in Taiwan.