For many archives working to publish collections online, securing copyright is a time-consuming challenge. What if the labor-intensive process of copyright outreach could be designed to increase the yield of staff time and add value to collection metadata? This case study explores an effort at the Irwin S. Chanin School of Architecture Archive of The Cooper Union to combine copyright outreach with author-generated metadata in an attempt to address common architectural record cataloging challenges. Specifically, the study looks at direct correspondence with creators as an opportunity to both secure permission to publish copyrighted materials and to fill descriptive holes in subject, title, caption, image orientation, and authorized name. This article further studies the feasibility of combining two laborintensive processes, discusses a preliminary and revised workflow, and evaluates the practicality and value of corresponding with over eight hundred individuals.