In this article, I highlight the emergence of a cosmopolitan turn in Literature education as observed in teachers' beliefs and practices in Singapore schools. Central to the cosmopolitan turn is the view that Literature education should not be disengaged from real-world connections to others particularly those who are marginalized and oppressed in the world. In the first part of this article, I describe core principles informing a cosmopolitan approach to teaching Literature that is distinct from previous movements. In the second part, I utilize case studies of Literature teachers from four secondary schools in Singapore to discuss key tensions resulting from teachers' attempts to foster cosmopolitan sensitivities. These tensions point to the propensity for Literature education to prioritize a form of universalism that neglects the dynamic interconnections between national and global identity; to encourage a human capital approach to education where cosmopolitanism is co-opted to strategically benefit elites and to perpetuate passive rather than active cosmopolitan engagement with justice. I suggest that awareness of these tensions can enable educators to develop more holistic and ethically grounded cosmopolitan Literature education where all students can be equipped with critical and empathetic capacities to navigate diverse and conflicting values in our global age.