In stability, security, transition, and reconstruction (SSTR) operations like the U.S. mission in Iraq, negotiation is a common activity. The success or failure of the thousands of negotiations taking place daily between U.S. military officers and local civilian and military leaders in Iraq affects tactical and operational results and the U.S. military’s ability to achieve American strategic objectives. By training its leaders, especially junior ones, to negotiate effectively, the U.S. military will be better prepared to succeed in the increasingly complex operations it is conducting—in Iraq as well as the ones it will face in the new strategic environment of the 21st century. This monograph analyzes the U.S. Army’s current predeployment negotiation training and compares it with the negotiating experience of U.S. Army and Marine Corps officers deployed to Iraq. The author argues that successfully adapting to the nature of the contemporary operating environment requires changes that include increased training in negotiation. Based on interviews with U.S. officers, the author identifies three key elements of negotiation in SSTR operations and offers recommendations for U.S. soldiers to consider when negotiating with local Iraqi leaders; for U.S. military trainers to consider when reviewing their predeployment negotiation training curriculum; and for the Army and Marine Corps training and doctrine commands to consider when planning and structuring predeployment training.