The Virtual Library Project1 at the Naval Surface Warfare Center/Carderock Division (NSWC/CD) is being developed to facilitate the incorporation and use of library documents via the Internet. These documents typically relate to the design and manufacture of ships for the U.S. Navy Fleet. As such, the libraries will store documents that contain not only text but also images, graphs and design configurations. Because of the dynamic nature of digital documents, particularly those related to design, rapid and effective cataloging of these documents becomes challenging. We conducted a research study to analyze the use of expert systems and intelligent agents to support the function of cataloging digital documents. This chapter provides an overview of past research in the use of expert systems and intelligent agents for cataloging digital documents and discusses our recommendations based on NSWC/CD’s requirements.