Automation is a defining feature of today’s societies—not only since ChatGPT and generative artificial intelligence (AI) have accomplished to produce yet another wave of hype. This essay introduces a special issue on automation and communication in the digital society. It aims to study how subjectivity, agency, and empowerment become defined and reconfigured in novel human–machine encounters and, more broadly, in societies which in large parts are kept going and sustained by complex digital infrastructures. The issue includes contributions from a wide array of disciplines and perspectives and engages with conditions, contexts, and consequences of automation in very different settings ranging from journalism to self-service hotels, and from social movements in Hong Kong to the Russian Invasion to the Ukraine. The articles offer critical perspectives on the transition of human activity into machine operations, and back, as well on the social dynamics changing and emerging in increasingly digitized and datafied societies.