This chapter explores how Taiwan is seeking to follow a pragmatic approach towards both India and China, as it faces several dilemmas in its everyday foreign policy decisions. From taking a stand on India–China territorial disputes to managing the New Southbound Policy, Taiwan meets several crossroads. The perspective is shaped by the Doklam stand-off in June–August 2017. Although Taiwan’s media outlets are often criticized for carrying far too little international news coverage, the dispute has in fact attracted the intense attention of Taiwan’s media. Interestingly, differing and even contradictory viewpoints can be found from the Taiwanese press. Against this backdrop, this chapter aims to illustrate Taiwan’s historical and contemporary position on the China–India boundary dispute. The specific focus is on how the China factor and policies such as the New Southbound Policy are portrayed in shaping Taiwan’s attitude towards the issue as Beijing and New Delhi are still embroiled in the border dispute. The chapter argues that Taiwan’s position over the China–India dispute is more associated with its perception of China than its relationship with India.