This paper analyzes the direction and scope of Taiwan’s foreign policy by the government of Tsai Ing-wen. After critically assessing Taiwan’s new diplomatic and trade efforts under the umbrella of the so-called Warm Diplomacy, it is argued that although its new strategy reflects a policy shift that can potentially broaden and diversify Taipei’s international possibilities, its highly ideological burden, democratic ambiguity, in addition to the ever problematic trade dependence, pose challenges and shadows for Taiwan’s effective external extraction and validation in the medium term.