This chapter examines the attempts by the first Obama Administration to reach out to Iran in an effort to build trust. It traces the failure of Obama’s diplomatic efforts to secure any reciprocation from Iranian leaders. The lack of reciprocation shows the problem of accurate signal interpretation when there is no trust. It focuses on the negotiations in 2009–10 over limiting Iran’s supply of nuclear fuel in return for refuelling the Tehran Research Reactor. The chapter argues these negotiations failed because of the lack of trust. What makes this case so important is that there was no face-to-face interaction, which this book argues is critical to the development of interpersonal trust and accurate signal interpretation.