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This paper scrutinizes a gap in our historiographical imagination between the anti-imperial foment of the Age of Revolutions and an age of international Caribbean activism in the twentieth century. Nationalist historiography has often omitted or suppressed many popular stories of solidarity on the island of Hispaniola or Haiti at mid-century, even as it was home to the only independent island states in the Caribbean. Trujillo-era authors caricaturized the period as one of relentless conflict between the two states, and a paucity of writing has made revision of that narrative difficult. Nevertheless, regional plans for independence and federation accelerated in 1850s and 1860s, fed by the threat of encroaching capital, shifting labor modes, and new technologies. Dominican and Haitian would-be reformers collaborated extensively in the mid-nineteenth century, as these questions of sovereignty became urgent. The paper explores the logic, extension, and shifting bases of these cross-island solidarities, as well as how they have been silenced in subsequent literature. Often fractured from or in opposition to local island governance, these philosophical traditions are at the margins of nationalist rememberings of the era. Their ambitious imagination for alternative economic and political futures offers not only the seeds of pan-Caribbean federalist thinking in latter decades but also whole new contours of Dominican and Haitian history.