Examining the transition from slavery to free labor through the lens of the overseer-state, this chapter clarifies the ascent of labor regulation to a key preoccupation of colonial rule, reveals plantation colonies as sites of experimentation in interventionist governance, and illuminates the evolving relationship between colony and metropole (and different colonies to one another). The analytical framework of the overseer-state also demonstrates how the changing character of colonial labor management entangled British and Continental European modes of imperialism, complicating our historical understanding of the role played by liberal ideology in British imperial governance and political discourse. The overseer-state, concretely and conceptually, bridged the histories of the British Empire and the French, Spanish, and Dutch Empires, revealing how the development of labor control mechanisms in Britain’s plantation colonies remained a European enterprise rather than merely a British one.