The study of the relationship between copyright and creativity is a core research program in the field of cultural economics (Weber 2017, Bille etal. 2020). Another part of the canon is that artists gain psychic income from moral rights when a work of art is identified with its creator, whereas exercising legal rights facilitate revenue streams and economic income (Towse 2001). We observe that there may be a tension between psychic income and economic income especially in the digital economy where the cost of the reproduction of a musical work can approach zero. Our research question is, “when might the strict enforcement of music copyright not be rational?” Entrepreneurial decisions about copyright enforcement are a case of cost-benefit analysis at a given place and time with subjective attitudes and perspectives about future risk and return. Given the radical (Knightian) uncertainty in entrepreneurship, we find that the case study approach is a good method to explore the many unexpected opportunity costs by using a specific not-for-profit arts organization in the US as the “firm” for analysis. The Reggae Sunsplash Preservation Society was formed five years ago to catalog, restore, digitize and disseminate around 200 hours of analog film recorded at the Festival in Jamaica during the years 1978 to 1994. The operating motto of the filming process for the Festival producers was “third-world music with first-world technology.” Artists were offered profit-sharing or a performance-based fee in cash for the rights to the recorded performances, 90% of the artists accepted the cash option. The rights to these performances fall to one of the founders of Festival and now director of the preservation society (Abbey 2021). Many of these performances have been bootlegged with inferior quality on YouTube, some with millions of views. Given time and resource constraints the firm faces value trade-offs in pursuing copyright enforcement for these bootlegged performances. For example it may mean that enforcing rights would mean less bootlegs, and therefore less “views” and less moral rights (and potentially more economic income over the longer term) for the foundational artists who appeared at the Festival. May in fact bootlegs be a form of brand marketing? Our research explores this and other questions and concludes that a situation-specific transactional cost approach may help shed light on the management of music copyright along the stages of production (Throsby 2008).