This project examines the ways in which infrastructure leaves its mark within contemporary Caribbean cultural representations. Roads, electrical grids, networks, and nuclear plants become dynamic sites for reflecting on the political, economic, and social issues facing the region at the turn of the twenty-first century. Within a selection of literature and visual culture from the Greater Antilles, I explore the tension between political discourse and material reality, analyzing the promises that infrastructures represent and the embodied experiences of their intended beneficiaries. This exercise ultimately points to the persistence of colonialism in the region, from the aftermath of Cold War developmentalism to the consolidation of aid and debt as forms of global coloniality. Building upon work by sociologists, anthropologists, and geographers in the growing field of critical infrastructure studies, I develop a methodology for analyzing infrastructure within literature. In addition to literal representations, I examine the diverse ways in which it leaves its mark on the text. I look to setting, characterization, and narrative structure. I explore the ways in which roads, electricity, and water appear through metaphor and metonymy, as well as in rhythm, affect, and imagery. In this way, literature can contribute a unique perspective to critical infrastructure studies. In the first chapter of this dissertation, the lasting impact of modernization in Puerto Rico manifests itself within literature and visual art through the breakdown of transportation, the electrical grid and, more recently, the financial impasse of an unpayable debt. In the second chapter, I consider speculative fiction that extrapolates emergent technologies within a Caribbean setting. Yoruba and Taino deities play a key role, merging with IT technology and staging a complex investment in the future. Finally, in the third chapter, I dissect representations of stalled initiatives. I highlight the ecosystem of people, things, and ideas that condition the outcome of projects like a Soviet-funded nuclear plant in Cuba or post-quake reconstruction led by the international community in Haiti.