Pervasive technologies are enabling an increasingly data-rich world that is mediated through a broad spectrum of often highly interdependent systems. The data science surrounding these systems is rapidly transforming nearly every aspect of our lives. But how trustworthy are the systems and data upon which we have come to rely? This article explores the complex collaborations and interdependencies that mediate trust-formation and examines six challenges in generating and sustaining trust in the context of data-rich systems.