After the victories at Yarmuk and Damascus, Abu ʿUbayda ibn al-Jarrah ﵁ marched south to lay siege to the last great stronghold of Byzantine Palestine. Jerusalem stood on a plateau of seven hundred fifty meters, enclosed by three valleys. The Tyropoeon in the east, the Hinnom in the south and west. The city walls were old but massive; the gates — Damascus in the north, Jaffa in the west, the Dung Gate in the south, the Lions’ Gate in the east — were manned by Byzantine garrison troops.
Abu ʿUbayda ﵁ chose a methodical encirclement rather than a direct storming assault. He set up his headquarters about two kilometers south of the city, in a siege camp with good water and a view of the southern gates. Three Muslim corps were positioned in a half circle around the western and southern approaches. The northern route to the Byzantine hinterland was sealed off by cavalry, so that no food or reinforcements could reach the city any longer.
Early attacks on the southern gates, the Dung Gate in particular, were repulsed. The Byzantine defenders loosed volleys of arrows and stones from the walls, and the slope up to the walls was so steep that a storming assault became impossible without heavy losses. Abu ʿUbayda ﵁ withdrew his corps and concentrated on starving the city out.
The siege lasted through the winter. Food stores in the city dwindled slowly. The Byzantine emperor could send no relief; after Yarmuk his army in northern Syria was no longer capable of offensive operations. The defenders of Jerusalem gradually realized that they stood alone. In the spring months, voices within began to argue for negotiations.