This paper reports on a work-oriented design project concerned with the question of how to migrate shared, workgroup document collections currently kept on paper online. Based in a civil engineering workgroup, the focus of our project is a document collection called the “project files”, a heterogeneous mix of documents that serve as an ongoing resource for the group during a project's course as well as an archival record at its completion. We describe the dynamics of the standardized classification scheme in use for the project files, existing practices of document filing including routine troubles, and the prototype developed to move the project files online. The latter includes a configuration of hardware and software along with associated practices of document scanning, coding and search. We conclude with some reflections on the difficulties of maintaining alignment across paper and digital media in the migration to online document collections, and with a summary of the questions posed and answers provided by our project.