This chapter examines the post-Six-Day War period and the challenges faced by Moshe Dayan, particularly in governing the West Bank and Gaza Strip, home to a significant Palestinian population hostile to Israel. Dayan grapples with the complexities of governing non-citizen residents and contemplates the future of the occupied territories, seeking a final arrangement with the Palestinians and the broader Arab world. The chapter also sheds light on Dayan’s experiences in Vietnam, where he gained insights into the challenges faced by the US military. He would use his experience in Vietnam later on in his career. Dayan’s observations on the need for precise intelligence, the importance of winning hearts and minds, and the struggle against Communist ideology offer valuable lessons for military strategy. Additionally, the chapter explores Dayan’s personal experiences, including his profound connection to the historic sites of Jerusalem and his recognition of the need for intense work to regulate the complex situation in the region and preempt potential conflicts.