My project focuses on the preoccupation in contemporary Caribbean novels with the memory and afterlives of indentured labor, supplied from colonial India to the West Indies between 1838 and 1917. I argue that such works, when treated alongside archival documents that focus on indenture, throw into relief deep ambivalences in colonial ideology, and contribute to the postcolonial and critical race studies endeavor of making visible the various ways that European liberal ideas of "freedom" and "modernity" relied on unfree and connected forms of labor and migrations, such as indentured labor and slavery. In particular, my dissertation contends that the imaginative space and form of novels read with colonial reports, correspondence and journalism helps to demonstrate two important transnational "intimacies," following Lisa Lowe, or entanglements, that colonial logics have long obscured. The first is that between indenture and slavery, which I argue have separate but palimpsestic histories, and which I suggest Caribbean writers often recognize the political utility of in reactivating cross-racial solidarity. The second "intimacy" I call attention to is that between colonial India and the Caribbean through the reciprocal relationship between early twentieth century Indian nationalist efforts towards anti-indenture campaigns and ideas in the West Indies concerning indenture. Both transnational relationships largely become visible through contrasting representations of Indian indentured or "coolie" women, which I analyze by tracking the production, animation, and mobilization of the coolie woman trope in the archive as morally depraved, how this trope is taken up and in part subverted in Indian anti-indenture campaigns, and how contemporary feminist novels reject and reimagine coolie women's lived experiences.