Advocating for art disciplinary methodologies in collaborations with digital collections librarians, especially in academic libraries, is a vital skill. While art librarians have refined and transformed their relationship to art disciplines in practice and through professional organizations like ARLIS, communicating the importance of art methodologies to their generalist colleagues in digital collections can be challenging. This disciplinary disconnect can result in collaborations and digital projects that fail to meet the needs of the art community because they do not include the necessary information used by art researchers and, thus, thwart discoverability. However, successful collaborations are possible with compromise and negotiation. The Shields Trade Card Collection, housed at Walter Havighurst Special Collections and University Archives at Miami University, serves as a case study, demonstrating both the need for art librarians to advocate for art specific methodologies throughout the lifecycle of a digital collections project while identifying specific areas of compromise key to sustaining future collaborations.