In this talk I attempt an intimate and immersive story of the meanings of indentured labor, plantation capitalism and mediated life through a focus on shipwrecks. Some of the most enduring mythographies of tropical islands derive from an 18th century French romance novel, Bernardin de Saint-Pierre’s Paul et Virginie (1787). It describes the idyllic childhood of two white European children who grow up in Mauritius and tragically perish in a shipwreck. Drawing on this story and its spin-offs, I consider a cultural and mediatic history of shipwrecks and the material things that spill out from them. Paper, wood, oil, metal, flesh, and bone; each of these things carries media histories of meaning-making be it as carriers of human cargo (wooden ships), instruments of commercial exchange and colonial bureaucracy (paper currency, paperwork), or as inscriptions of racial, gendered, and caste violence (drowned bodies). From such a vantage point, when the bulk carrier ship MV Wakashio ran aground off the coast of Mauritius in July 2020 it allowed a momentary flash of historical and cultural insight into the entanglements of imagined islands, colonial trade routes, neo-imperial commodity traffic, and the lives of fish, coral, and islandic humans. My methods in this talk are inspired by what might be called the diagnostic logics of cultural theory as practiced by Siegfried Kracauer and Walter Benjamin, with their pursuit of symptoms and surfaces.