At some point in their careers, library administrators will likely be involved in the acquisition of a new library automation system. Whether it is a first-time acquisition or a migration from old to new, the decision is perhaps the most challenging the administrator will ever have to make. Despite an abundance of information in the library literature on the mechanical and managerial aspects of acquiring a new automated system, there is scant information on, or investigation into, the decision-making process that leads to the selection of an automation vendor. Based on the premise that the automation decision is both complex and risky, it is a decision fraught with ambiguity, uncertainty, and conflict. This study offers exploratory research on the automation decision process and those factors that lead to decision difficulty. Using the Garbage Can Model of Organizational Choice as a theoretical framework, this study uses decision resolution as a criterion of decision success. Based on research to identify factors that have enabled decision makers to achieve resolution, the authors of this study seek to make recommendations that will enable administrators to better manage a tough decision.