The chapter provides a transnational perspective on how the apprenticeship’s end caused new challenges for the free labor experiment, as British West Indian colonial economies faltered in the 1840s and former slaves asserted their rights as working people. In their pursuit of expanded liberty, black West Indians forced American antislavery to examine the limitations of a strict free labor ideology, and to envision the experiment’s success on other terms, as the issue of slavery moved to the center of national politics.