This dissertation locates a pre-history of modern material alienations in colonial Spanish America. Alienation is often understood as a modern phenomenon, the byproduct of exploitation under industrial labor or the crisis of the individual in the face of the strictures of modern society. Colonial actors, however, sensed, internalized, and expressed an understanding of and frustration with their material marginalization in the face of an ever-intensifying colonial economy that rewarded the landowning benefactor class at the expense of the diverse residents of the colonial world. Focusing on the literature, visual culture, and hagiography of mid-colonial Peru, these alienations appear and reappear in varying discourses of isolation, marginalization, and outsideness (enajenación in early modern Spanish) extending to indigenous, Spanish, and Afroperuvian subjects. In each case, land and labor are at the center of these forms of primitive alienation, causing diverse subjects to feel that the economic climate and conditions of work and worship have led the world around them to become unrecognizable, unfamiliar, and ultimately meaningless. Reading the works of Spanish colonial chroniclers, satirist Mateo Rosas de Oquendo, indigenous chronicler Felipe Guaman Poma de Ayala, and the hagiographers of Afroperuvian saint Martín de Porres as expressions of enajenación that anticipate later theorizations of alienation, I argue that as primitive accumulation anticipates capitalism, diverse colonial primitive alienations (from lands, community, spirituality, and history) arise in anticipation of the alienation of the industrial worker. This pre-history makes patent the modernity of colonial subjectivities to suggest that affective responses to the colonial enterprise mark the onset of the modern individual.