We are in a critical moment because many materials from the colonial and imperial archive are being digitized. I therefore propose a session to talk about if and how we can avoid reproducing the colonial structure of existing historical archival materials as they are migrated into digital archives. Further, I would like to discuss how to integrate this question into the classroom and to use as an example an assignment that I developed with colleagues in Caribbean studies and librarians at UF. In this assignment, students analyze a historical photograph which has minimal metadata, place it in its historical context, analyze its existing metadata and make suggestions for enhancing that metadata in ways that would counter the limitations, particularly the colonial assumptions, implicit in the existing metadata. Students analyzed photographs from the Panama Canal Museum Collection, which might well be described as an imperial archive as it contains the materials collected by the white US employees of the US Canal Commission. Many of these photographs document the construction of the canal and in so doing include images of Afro-Caribbean workers; however, the workers are rarely mentioned. Students added subject headings and notes to the catalog record to identify the Afro-Caribbean workers and explain the context of their labor. Students have found this assignment rewarding because they see that their work can change how the subjects in the photographs are defined. The photographs were listed under construction (“The Gatun Locks,” “Widening the Pavement in Panama City,” etc.); with new subject headings and notes, they can be found by researchers looking for race, labor, and Afro-Caribbeans in Panama. The Students have all signed permissions for their work to be included in the dLOC/UFDC catalog records and their work will be included in the UFDC metadata where relevant.