In 1839, the year after slavery's end in the British West Indies, a group of young abolitionist graduates of Ohio's Oberlin College established a Protestant mission in Jamaica. Joining the already numerous British missionaries on the island, these mostly Congregationalist white American men and women created mission churches and schools to aid and convert black Jamaicans as well as to show skeptical whites in the United States a successful model of an emancipated society. The fledgling American Missionary Association adopted their project in 1847, and it continued until the end of the American Civil War. The mission failed to be the shining example of an interracial society its founders had intended because in spite of their devotion to their doctrine of Christian liberty, the missionary men and women positioned themselves as perpetual parents over "childlike" Jamaican converts. The dissertation focuses on the conflicts over the meaning of liberty as different factions in the mission defined it. It does this in two parts: first by showing how abolitionist men committed to liberty instituted mission churches and households based in strictly controlled hierarchies, and second, by examining the challenges brought to those hierarchies by black Jamaicans, white women, and others. The Americans went to Jamaica with an idea of Christian liberty that conflated religious conversion and emancipation. When the missionary men found that few black Jamaicans lived up this initial expectation of a "born again" society, they managed this "licentiousness" by imposing strict church discipline and by becoming increasingly attached to their power as infallible "fathers" overseeing their mission households. Over the course of the mission's almost thirty-year history, disgruntled members of the mission---both black and white---challenged this hierarchy in direct and indirect ways, and most interestingly, the ministers could, at times, be convinced that they were wrong, especially when a white man had raised the complaint. Black Jamaican men and women and the mission's white women had less success. Occurring as they did in the missionary setting, these periodic disputes over the mission's power structure reflected and distorted American discussions about gender and race, religion, and Christian reform.