This special issue of Organization aims to extend the critical debate on the impact of digital technologies and internet firms on organizations and organizing. Today, the link between digital technologies, the increasing power of internet firms, and the accompanying power shifts in and around organizations is not well understood in theoretical or empirical terms. The responsible guest editors invite scholars to explore the ‘dark’ and the unexpected sides of digitalization, i.e. issues that have been (so far) overlooked, ignored, or suppressed in regards to the digitalization of organizations and organizing. The further exploration of the dark and unexpected sides of digitalization is one that is well suited for cross-disciplinary research and for thinking critically beyond established boundaries. Scholars from various disciplines are welcome to submit manuscripts that engage with critical organizational research. The political and ethical implications of digitalization on organizations and organizing can be analyzed on multiple levels.