Public and academic opinion remains divided regarding the benefits and pitfalls of datafication technology in organizations, particularly regarding their impact on employees. Taking a dual-process perspective on trust, we propose that datafication technology can create small, erratic surprises in the workplace that highlight employee vulnerability and increase employees’ reliance on the systematic processing of trust. We argue that these surprises precipitate a phase in the employment relationship in which employees more actively weigh trust-related cues, and the employer should therefore engage in active trust management to protect and strengthen the relationship. Our paper develops a framework of symbolic and substantive strategies to guide organizations’ active trust management efforts to (re-)create situational normality, root goodwill intentions, and enable a more balanced interdependence between the organization and its employees. We discuss the implications of our paper for reconciling competing narratives about the future of work and for developing an understanding of trust processes.