Digitalization has far-reaching implications for individuals, organizations, and society. While extant management and organization studies mainly focus on the positive aspects of this development, the dark and potentially unexpected sides of digitalization for organizations and organizing have received less scholarly attention. This special issue extends this emerging debate. Drawing on empirical material of platform corporations, social movements, and traditional corporations, eight articles illuminate the various negative implications of the digitalization of work and organization processes, particularly for workers, employees, and activists. In this introduction, we contextualize these valuable contributions that underline the dangers of the ubiquity and simultaneity of digitalization and begin to sketch out potential avenues toward a comprehensive critical agenda of digitalization in organization studies.