This first chapter traces how the emergence of free soil in Sierra Leone, Haiti, and Liberia captured the attention of American reformers in the early nineteenth century amidst growing concern about free African Americans’ social welfare and economic prospects in the United States. Reformers, activists, and potential migrants debated whether the migration of free and recently freed black men and women would improve or degrade the conditions of individual migrants, whether it would help or hinder the black communities left behind, and whether it would positively or negatively affect the overall progress of general emancipation. Reviewing the information available to them, they debated whether to encourage the voluntary “emigration” of free people to Haiti, to support the typically involuntary “colonization” of former slaves to West Africa, or to oppose free-soil relocation schemes altogether. In the process, advocates of each position honed their ideas of what freedom meant, where it could be achieved, and who could enjoy it.