This chapter analyzes the United States use of psychological warfare to win the hearts and minds of the people of Indonesia during the 1950s, and Iraq and Muslim majority countries in the aftermath of the 9/11 attacks. This chapter explains both the change and historical development of U.S. psychological warfare, the agencies involved, and the policy options at its disposal. It argues that the U.S. uses of psychological warfare without clear understanding of the domestic politics of the targeted country produced results that were not only harmful to the people of the country targeted but also to U.S. interests. Drawing from the past and present practices of U.S. psychological warfare this chapter seeks to identify the changes in U.S. psychological warfare, and the mistakes that the U.S. has made, as well as the type of challenges that it will face in the future.