In the digital era, trust is a key concern. This chapter introduces a digital era interaction (DEI) matrix to explore trust relationships at multiple levels: between individuals, individuals and organizations, and between organizations. It considers each of these interaction aspects in turn; it draws on recent research projects as examples, and develops a common set of themes. The chapter concludes by identifying areas for further research that will help to advance our understanding of the role of trust in inter-organizational and interpersonal virtual interactions. It argues that such research is necessary if organizations and individuals are to benefit fully from the potential and the promise of virtually enabled interactions.