The main argument of this article is that the transformation of the upper secondary education system in Taiwan in the past decade has shown a shift from the 'insular institutional, individual curriculum' model to the 'connective institution, flexible curriculum’ model. This transformation includes the integration of upper secondary education in two main dimensions. First, the vertical integration refers to an increased corporation between upper secondary education and both higher education and lower secondary education. Second, the horizontal integration indicates a more unified, interactive and corporative relationship between general and vocational education. These different aspects are then discussed and the issues arising as a result of these developments are also analysed. In addition, drawing on the distinction between divisive and connective specialisation and the distinction between tracked, linked and unified system, it is argued that the concept of connective specialisation and the linked system can be used to highlight many features of the 'connective institution, flexible curriculum' model. According to these analyses, this article concludes by suggesting that the transformation of the upper secondary education system in Taiwan towards a 'connective institution, flexible curriculum' model has become increasingly evident in the last decade. The main theme of this transformation is to take 'connective specialisation' as a new form of educational specialisation and to increase the overall flexibility of upper secondary education in terms of programmes / curriculum and pathways.