As cultural service organizations increasingly integrate digital technologies, they face critical challenges in maintaining their authenticity—a concept deeply rooted in their traditional practices. This study explores the negotiation of authenticity within cultural organizations as a function of value co-creation. In line with the interactionist perspective on authenticity, we approach authenticity as the outcome of ongoing interactive negotiations. Viewing authenticity through the negotiation lens offers a fresh perspective on the context-specific dynamics of value co-creation. The study builds on a qualitative study of the Royal Swedish Opera, during the transition from de-institutionalization phase to re-institutionalization phase of digitalization. We conducted semi-structured interviews with 25 employees in various key positions, from administrative staff to artistic leadership. Our findings reveal that authenticity is negotiated among various actors in three dimensions concerning Historical Continuity, Artistic Commitment, and Social Commitment. The study sheds light on how negotiations are essential to the emergence of new solutions and novel comprehensions of authenticity and value. Using Hegel’s dialectics, this chapter demonstrates how a synthesis emerges as a resolution to the paradox of honoring tradition while pursuing innovation. Importantly, our study highlights the need to understand digitalization in the light of forces present at the different levels of the ecosystem, and the necessity to view digitalization as the means to renegotiate organizational and societal goals.