In this dissertation project, I make three separate contributions to the study of the political economy of automation which center the agency of workers and society over technological change. The papers presented here each take a historical approach, both to contextualize modern debates over new technologies and to describe political responses that may have fallen out of contemporary awareness. In the first paper, I examine the origin of the term “automation” to reveal the ways that this concept has been shaped by social and political imperatives. I then propose a new definition and conceptualization of automation which respect this reality and open new avenues for research into this form of technological change. In the second paper, I examine the role played by the occupational structure of unions in determining their responses to automation. Drawing on a comparison of the cases of 1) the AFL-CIO and its Industrial Union Department and 2) New York Typographical Union No. 6 from approximately 1950–1975, I show that industrially-organized unions are more receptive of automation than are unions organized along craft lines. In the final paper, I examine the role that the different approaches to labor force control adopted by craft unions play in shaping both their responses to new technologies and their inclusion or exclusion of women workers. Through a comparison of the histories of the typographical unions in the United States and the United Kingdom over 150 years, I show that unions adopting an apprenticeship-based system of labor force control are both more resistant to new technologies and more exclusionary of women than are unions adopting a strategy of incorporation. Taken together, these papers show that workers and unions have been neither helpless cogs nor implacable wrenches in the machinery of technological change.