Of all of the cities that fell under Jordanian control as a result of the Palestine War in 1948, Hebron and Bethlehem came under special circumstances in 1948-1949 due to the vagaries of war. During the fighting, the Arab armies had little organization among themselves in defending Palestine against the forces of the newly established state of Israel. Egypt had both its regular army and unofficial forces of the Muslim Brotherhood in Palestine, including in Bethlehem Hebron, and Jordan had its Arab Legion forces in the country. These two states both ended up occupying these two important southern Palestinian cities, by 22 October 1948, after segments of Egypt’s forces got cut off from the rest of its army following an attack by Israel on Egypt’s positions in the Naqab at which time Jordan’s forces came to help stabilize control over those cities. The result came to be called the “Dual Era,” or, in Jordanian documentation al-‘ahd al-thunā’ī. This arrangement was unusual to these cities, indeed, seemingly unique in all of Palestine. Each country competed for the backing of the Palestinian population, the latter left without a local leadership and stuck between two countries vying for control in cities where war with Israel seem to have been only one priority. Their control also seems to have extended to Bi’r al-Saba`, but, based on the writings of Jordanian, Palestinian, and Egyptian chroniclers and Palestinian diarists of the period, as well as Jordanian documents, the sources examined in this paper, Hebron seems to have been the focus of the military and political administrators. This study explores the Dual Era in Hebron, which lasted until May 1949, and Jordanian-Egyptian relations vis-à-vis each other and the Palestinian population over which they ruled. The paper also examines how the bureaucracy might have functioned during this uncertain period, which followed the British Mandate-era during which Palestinians staffed the administration. The very title of “Dual Era” suggests that there might have been collaboration and cooperation with two militaries and two military governors overseeing Hebron. Preliminary analysis of the sources, however, demonstrates tension more than cooperation between the two ruling entities in Hebron, a sentiment transmitted to the indigenous Palestinian population who felt they had to take a side in this charged environment.