This paper seeks to explore and explain the process through which Taiwan utilizes free trade – both at multilateral and bilateral levels – in enhancing its shrinking de facto sovereignty against the backdrop of ubiquitous `China factor’ in the twenty-first century. It argues that China’s sinicization project creates a scenario wherein increasing cross-strait stability ironically leads to decreasing de facto sovereignty for Taiwan. Due to this existing cross-strait security dilemma, Taiwanese leaders are being forced to preserve the island’s quasi-independent statehood due to fears of losing its remaining de facto autonomy over domestic and foreign affairs. In essence, Taiwan chooses to be de facto free by remaining de jure unfree. Taiwan’s sovereign space, therefore, becomes a pivotal referent object of its national security policy and strategy. Balancing between the two paradoxical interests of enhancing sovereignty while maintaining the Chinese-dominated cross-strait status-quo underlines the relentless games, changes, and fears that Taiwan confronts today.