Using Malmö Turism-a tourist bureau in the south of Sweden-as a case, this chapter examines its digital transformation; from being based foremost on promoting storytelling of real-life interactions with a few expert assistants at a physical tourist bureau, towards becoming a primary digitally based cross-and transmedia operation, where support of the hosting relied on a larger number of connected media and actors. Based on interviews with the organization before and after the reorganization, the chapter analyses the drivers, determinants and challenges that faced the organization during the transformation. It contributes with insight and understanding from a novel case that other tourism organizations may contrast their findings with, a challenge many of them are likely to embrace in the future.