Region is a dynamic concept dependent on particularities of space manifested through varying imageries, and South Asia is no exception. As a regional category, it was borne out of the USA’s need to demarcate the post-War world according to its geopolitical interests, and since then, the elites of all South Asian states have unexceptionally found it difficult to shed off the realist lens vis-à-vis each other. Even though it’s an incredibly diverse region, there is a remarkable consistency in the way the dictates of sovereign territoriality have guided the nation-building projects of all states, and as a result, alternate ways of imagining the region have been severely compromised. South Asia, therefore, remains one of the least integrated regions in the world despite carrying tremendous collaborative potential in various fields. In this context, this chapter explores the possibility of conceptualizing the region through the lens of Critical Theory, which focuses on the emancipatory project of human beings through an anthropological reading of identity and communities. It argues that for such an understanding to gain in prominence, the political culture of the region needs to undergo a fundamental transformation from the territorial, authoritative, and state-centric notion of power and control to a more empathetic, unfettering, and citizen-centric notion. However, it is easier said than done. The material realities of the region centered around the India-Pakistan rivalry, China’s inroads into the region, weakening of civil society institutions, and rise of majoritarianism and religious fundamentalism amidst growing economic distress have ensured that such a transformation is still some distance away. © 2023 selection and editorial matter, Šumit Ganguly and Frank O’Donnell.