This second issue of the Weizenbaum Journal of the Digital Society brings together four contributions that examine the role of actors and regulation in processes of digitalization from the perspective of different disciplines. The topics include the role of the Silicon Valley discourse on entrepreneurship in legitimizing a specific model of work in the IT industry, the particularities of the European platform regulation approach, the development and enforcement problems of copyright liability regulation in Germany, and the development and regulation of automation processes in the workplace.