While the literature on digital transformation is growing rapidly, we still know very little about the conditions of digital transformation in non-profit organizations in general and performing arts organisations specifically. This is especially true for organizational sensemaking processes, which take place in the field of tension between self-image, often strongly anchored in tradition, and a public mission. Based on a comparative case study of the development of digital offerings in performing arts organizations, identify six issue domains of sensemaking. Each issue domain is characterized by specific ambiguities that set the frame for sensemaking. The social constructivist approach of the study allows to enhance the existing digital transformation (DT)literature. Its strong focus on business process reorganization, strategy formulation, and technology deployment is complemented by highlighting serendipity, bricolage, and a digital condition as significant modes of DT in performing arts organizations.