What constitutes the legal environment surrounding and intersecting artists and arts administrators? In spring 2023, we set out to explore this question through a pedagogical and andragogical collaboration between Berea College’s Janis Ian Special Collection and the University of Kentucky’s Arts Administration course: Legal Environment of Arts Administration. Our overarching perspective was to consider how we could activate, leverage, and connect primary resources to the learning and development of future arts administrators. Our goal was to create an experiential learning environment that challenged students to discover the legal dilemmas embedded within and spanning across the professional career of a successful musician. This real-world legal understanding underscores critical decision making skill development needed by artists and arts administrators today. The Janis Ian Special Collection includes primary records such as contracts, copyright and licensing documents, compliance records, and industry correspondence pertaining to legal practices surrounding her career. During the one-day field trip to the special collection, students audited primary records in order to uncover and evaluate a variety of legal scenarios, provoking discussion around the role of arts administrators in the sustainability of an artistic career. The purpose of our study is to share how we planned, organized, and facilitated the field trip between our two universities, including the co-curricular development of applying archives to the classroom. Our collaborative aim is to develop an open educational resource guide outlining how to conduct these kinds of cross-institutional learning collaborations for other educators, librarians, archivists, artists, and arts administrators.