Digital technologies are not simply new tools to create and distribute copies of things; they also enable new social relationships through which people produce multiples. This thesis explores two examples of such digital systems: outsourcing paintings to the Chinese oil paintings industry, and crowdsourcing drawings using Amazon’s Mechanical Turk. Looking carefully at these socio-technical systems —which are both unique and underexamined in the art world—raises a number of interesting questions about authorship and human/computer relationships. This thesis does not propose to answer these questions, but the projects described are an attempt to explore the implications of these systems in various ways.