Freedom dues were typically payments of money, land, or clothing that masters gave to servants upon completion of servitude. Using case studies, this thesis captures the arc of a historic transformation in how freedom dues were perceived between the mid-seventeenth and mid-nineteenth centuries; it illuminates how these dues became a humanitarian symbol and the narrative of self-actualization that arose about them. The narrative focus on freedom dues was generated through tracts advocating immigration to colonial America and was integral to early understandings of the promise of New World prosperity. The texts I address use this narrative to critique a society failing to live up to its implied ideal: enfranchisement through hard work. My thesis reveals that often relations of servitude morph into something that looks dangerously akin to chattel slavery. In Chapter One, I contrast the Lawes and Libertyes (1648), where servants were to be prevented from "be[ing] sent away emptie," to the revisioning of this framework in the Fugitive Slave Law (1850), which enshrined slaves' perpetual indebtedness. In Chapter Two, I use the Records of the Salem Witch-Hunt (1692-93) to examine how Tituba's claim that the devil offered her an indenture followed by many "fine things" came to influence other testimonies. I argue that the narrative Tituba and others craft regarding the Devil's promise of servitude properly rewarded but not supplied by Massachusetts's governors would have been shocking in New England at the time. Chapter Three analyses The Scarlet Letter (1850) and reveals that, by presenting Hester Prynne as a branded, lifelong indentured servant, Hawthorne effectively portrays a variety of servitude that appears similar to black slavery. Hester and Pearl have their customary white privileges undermined, I argue, and Hawthorne's novel reveals abolitionist leanings. In Chapter Four, I consider Harriet Wilson's autobiographical text, Our Nig (1859). The Bellmonts' refusal to provide proper freedom dues to the novel's protagonist highlights the degree to which her servitude has been slavish, and Wilson's plea for support to remedy this wrong provides a final critique of "free" New England.