By the mid-nineteenth century, an archipelago of island prisons had come to span the globe, weaving together disparate sites, each existing separately within distinct imperial formations, yet connected through their shared punitive function . My research interrogates the contours of the penal archipelago at the level of global geopolitics, local prison societies, and political prisoners' individual experiences by examining case studies from Vietnam and Indonesia throughout the late colonial era and Cold War, namely Nusakambangan (Netherlands East Indies [NEI], Indonesia, 1908-present), Digul (NEI, 1926-1942), Buru Island (Indonesia, 1969-1979), and Con Son (French Indochina and Republic of Vietnam, 1861-1975). I argue that these prison islands constitute a distinct mode of punishment characterized by the application of a state's coercive power on subjects deemed politically dangerous that aimed to condemn them to social extinction rather than rehabilitate. Furthermore, these spaces have been instrumental to the making and unmaking of imperial and post-colonial authoritarian regimes. I use archival research and inter-textual readings of literature produced by political prisoners (novels and memoirs) informed by geographic theories of biopolitics to understand the historical conditions and processes that led to the creation of prison islands as well as how political prisoners challenged the very coercive power that immured them. Situated in this nexus of ambiguity cum excision, political prisoners seemingly expelled from collective consciousness, could suddenly through the power of literary imagination and political aspirations become elevated to national, and at times even global prominence. Thus, prison islands, though intended to extinguish political dissent, become sites of contestation over the relationship between the state and justice, propelling political prisoners to the forefront of public debates on the national and global stage.