The Herbert Simon Collection, which documents the life and work of the famous economist, is one of the most popular collections from the archives at Carnegie Mellon University. The physical collection was digitized in the early 2000s and the digital objects were managed using a homegrown collection management system. The system has since undergone several migrations. Links between physical items as well as the links between the physical and digital objects have been lost. Standards have not been applied, or have been applied inconsistently to the metadata that does exist. This lack of contextual information hinders the collection’s accessibility and usability. In the coming months, we will assess the state of the collection, understand its migration history, and finally develop a digital curation workflow to recover the lost information, reduce loss in future migrations, and make the collection more accessible. To accomplish these goals we have identified four key project aims including: 1) develop systems of labels to indicate and describe document availability, 2) establish clear file names and a naming standard to improve navigation, 3) make recommendations on collection structure and organization, and 4) map existing metadata to a standard. To evaluate our solutions, we will use “saticficing,” Simon’s own heuristic in which one must search through available options until a threshold of acceptability is met, or when an optimal solution cannot be found. Information loss in migration is inevitable; but we hope to “saticfice” the needs of our users while preserving Simon’s legacy.