This article explores the reasons for the dramatic change in Sunni Arab Iraqi attitudes toward the United States from 2004 to 2007, which made possible the “Awakenings,” local groups of mostly Sunni tribes and former insurgents that decided to cooperate with the United States against al Qaeda in Iraq. While there have been many studies of the military strategy, there has been little attention paid to the reasons for the underlying attitude change. This article argues that the dramatic changes in the information environment and in the nature of direct contacts across a range of Sunni society played a crucial role. It draws on a wide range of Arabic language primary sources that have generally been neglected in U.S. military-centric accounts. No single dialogue flipped the Sunnis, and the change would not likely have happened without the material changes underpinning their interests. But years of ongoing, intensive dialogues across a wide range of interlocutors reshaped the foundations of the relationship and to convince those involved individuals of the possibility of a strategic shift. American counterinsurgency (COIN) doctrine and the surge helped by proliferating the points of contact with Iraqis and by transforming the relations at the individual level. This has broad implications for key debates in contemporary U.S. foreign policy, as well as for counterinsurgency and international relations (IR) theory.