In the fall of 2011, The University Libraries of The University of North Carolina at Greensboro embarked on the digitization of a collection of approximately 250 historical scrapbooks that documented university history and spanned most of the twentieth century. This collaborative project brought together personnel from Digital Projects, Special Collections and University Archives, and Cataloging. Personnel faced a variety of challenges involving both technical and physical aspects of the project. Among these challenges were the deteriorating physical condition of the scrapbooks and the need to construct project workflows that would maximize efficiency and effectiveness in regards to both staff time and end product creation. In meeting and overcoming these challenges, project personnel came away with lessons learned in the areas of collaboration, communication, and appropriate workflows for a project of this type and scale. These lessons can be taken forward for application in other collaborative digital initiatives.