This chapter investigates how rapid digitalization, datafication, and platformization play out in public sector education at an upper-secondary level in Germany and Norway. Based on interviews and participant observations, I map how teacher unions understand and can prepare for such technological changes. I show that unions often are slow to react to new developments. Main obstacles are a lack of technical expertise and organizational resources. In addition, unions’ organizational power remains locked in national, regional, or even local frames while their opponents—in particular major tech companies, and consulting firms—operate at a transnational level and leverage their proximity to key decision-makers to initiate and implement disruptive changes at an increasing scale. As a conclusion I offer recommendations for new forms of resistance attempting to activate affordances of networked technologies for the advantage of labor organizations, employees, and citizens.