The advancing digital transformation of society creates a wide range of opportunities for improved access to information and resources that contribute to ensuring the availability of public services and the development of sustainable living spaces. This underlying potential does not only apply to urban areas; digitalisation projects are also being implemented in rural municipalities in order to exploit the potential of digital transformation. Nevertheless, the field of so-called smart regions has yet to receive substantial focus in research. To understand the specific challenges and enabling factors of digital transformation activities in urban-rural areas, a workshop was organised with the cooperation of municipal representatives of a model region in Schleswig-Holstein, Germany. Therein, specific technical, economic and social challenges as well as enabling factors of municipal digitalisation projects aimed at developing smart regions were identified. The results show that the success of digital transformation meas‐ ures in urban-rural areas is not only determined by the expansion of a corresponding technical infrastructure but in particular by the acceptance of citizens and municipality employees, as well as economic viability. This research further informs municipalities and future researchers on the critical factors required to effectively conduct digitalisation projects in the smart region context.