While the pace of digitization and its impacts on society and markets have become an independent topic of research and debate, far less is clear on how the traditional regulatory functions of governments should evolve with these transformative changes. In this article, we explain how technology disrupts the legal ecosystem and how an uncontrolled legal environment may provide carte blanche to techno-solutionism and cause disruptions that affect practices and society. In the face of uncertainty regarding the implications of fundamental rights and liberties at the core of liberal democracies, we outline two possible legal sustainability approaches, weak and strong, respectively. We do so by borrowing from the economic literature on environmental externalities and sustainability paradigms of economic growth. In this frame, we present a three-step process to align the order of rules with that of actions to create better conditions for a smooth and sustainable co-evolution between technological ecosystems and the prevailing institutions. Such a process aims at bridging information asymmetries by generating policy-relevant data, sharing knowledge among stakeholders to understand and make sense of such information, and creating opportunities for those ideas to turn into an “action” in the world of actions. In doing so, we strive for brokering knowledge between economic agents and regulators since only by having a shared common understanding of the state of affairs a shared normative view on the matter can follow.