The Health Sciences and Human Services Library holds in its Historical Collections dissertations required for obtaining the degree of Doctor of Medicine at the University of Maryland during the nineteenth century. A project to digitize these dissertations for inclusion in the UM Digital Archive began in 2011, thanks to an award from the National Network of Libraries of Medicine, Southeastern/Atlantic Region. This article presents challenges encountered, as well as rewards and learning experiences gained during this digitization project, especially in the assignment of accurate metadata, and in the assessment of scanning quality.