In this paper, I discuss the history of copyright’s development, highlighting the steady increase in control of copyright holders as well as explaining the limited protections extended to libraries and archives. I use several case studies to illustrate the role of risk management and its uneven success in the digitization of library and archival resources. Finally, I propose several alternative ways of addressing the challenge that copyright poses, including the suggestion that judicial lawmaking would be an effective way to clarify the applicability of the fair use doctrine.