In this chapter we argue that transparency is worthless in guaranteeing the trustworthiness of the trustees (those in charge of designing and managing digital systems) when trustors are vulnerable and depend on those same technologies and systems. Specifically here we focus on the trustworthiness of security engineers, those responsible for the dependability of systems and devices. We propose abandoning the rationalistic instrumental paradigm of trust to embrace a vision of trust as care in order to ensure the trustworthiness—that is, the competence, integrity, and benevolence—of operators of digitally mediated sociotechnical systems.