Countries are increasingly looking to ‘digitalise’ how public services are delivered, with welfare‐to‐work and public employment services being key sites of reform. It is hoped that digitalisation can achieve efficient, effective, and targeted services for those in need and there is now a growing body of research on both the opportunities and pitfalls associated with this transition to digital welfare states. However, as a concept, ‘digitalisation’ remains ambiguously defined, hindering understanding of the distinct ways that discrete technological innovations are reshaping citizens' access to social protection and the role of street‐level discretion in welfare administration. Drawing on interviews with expert informants from three countries pioneering digital reforms, this study aims to better understand what digitalisation entails for the delivery of activation. We identify three discrete modes of ‘digitalisation’ in welfare‐to‐work programmes: virtual engagement (remote activation), transactional automation (self‐activation), and digital triaging (targeted activation). Far from digitalisation heralding the automation and curtailment of frontline discretion, the different modes reshape frontline delivery and citizens' access to social protection in specific ways.