The concept of experiential learning is particularly useful when students are required to create database entries as part of an ongoing, real-life, online experience. A METRO grant in 2005 resulted in an opportunity to use students to create a CONTENTdm database, which, with the continued software support from METRO, has continued and evolved until the present. This case study chapter describes the experience of both faculty and students in the Queens College Graduate School of Library and Information Studies course entitled “Introduction to Digital Imaging.” Sections include a review of related literature, the background, technical issues, and implications for teaching, project procedures and workflow, successes and lessons learned, challenges, next steps, and emerging trends. Of particular interest is the use of out of copyright postcards and the metadata that has resulted from intensive student study and evaluation of the data contained on these cards. Those contemplating a digitization project of their own will be able to learn much about best practices, project planning, management, and the advantages/disadvantages of the CONTENTdm software.