Since the turn of the millennium, the field of global labor history has seen a flood of publications and the establishment of associations worldwide, contributing significantly to the renewal of labor history and history in general. After a brief introduction to global labor history, this article discusses some of its key issues, particularly the relationship between labor regulation and historical labor dynamics. These discussions critically evaluate the conceptual and historical tensions between free and unfree labor. This includes the tensions and historical significance of legal versus economic coercion and the relationship between legal theory and legal practice (law in action), particularly the use of judicial archives to study the limits and possibilities for workers, slaves, serfs, and indentured migrants to utilize the law. Finally, building on this, the article considers the huge debate on legal pluralism in labor relationships.