Siege of Emesa The Siege of Emesa was laid by the forces of Rashidun Caliphate from December 635 up until March 636 . This led to the Islamic conquest of Emesa , which was a major trading city of the Byzantine Empire in the Levant . Background . After a decisive victory at the Battle of Ajnadayn , the Muslim army conquered Damascus after a long siege in September 634 AD . The army continued their march northward and in late 635 AD , Abu Ubaidah ibn al - Jarrah sent Khalid ibn Walid with his mobile guard to begin the siege of Emesa and later joined him along the main body of the army . The Byzantine garrisons of Emesa and Qinnasrin made a truce with the Muslim army . It was agreed that Emessa would pay 10 , 000 dinar s and deliver 100 robe s of brocade and in return , the Muslim army would not attack Emessa for one year . If , however , any Roman reinforcements arrived to strengthen Emessa ' s garrisons , then the truce would become defunct . The gates of Emessa were opened as soon as the truce was signed , and thereafter there was free movement of Muslims in and out of the markets of Emesa , advancing the economies of major Byzantine towns . The garrison of Qinnasrin ( the ancient Calchis ) made the truce on the same terms . However , the governors of Emesa and Qinnasrin made the truce for reasons of expediency . Both hoped that their garrisons would be reinforced by Emperor Heraclius , and as soon as that happened they would repudiate the extortion of the Muslims . Muslim armies raided many cities in northern Syria , as well as the major towns of Hama Shaizar , Afamia ( known today as Qalatul - Muzeeq ) and Al Ma ' arra ( now Ma ' arrat - un - Numan ) . One by one , each city and town that fell to the Muslim army surrendered in peace and agreed to pay the jizya . It was while the Muslims were at Shaizar that they heard of Byzantine reinforcements moving to Qinnasrin and Emesa . This , naturally , led to the invalidation of the truce established by the city of Emesa . The arrival of winter gave the Byzantine garrison a further assurance of success . In their forts they would be better protected from the cold than the Muslim Arabs , who were not used to intense cold , and with only their tents to give them shelter would suffer severely from the Syrian winter . Heraclius wrote to Harbees , the military governor of Emessa , " The food of these people is the flesh of the camel and their drink its milk . They cannot stand the cold . Fight them on every cold day so that none of them is left till the spring . " The siege . Abu Ubaidah decided to take Emesa first , and thus cleared his rear flank from the enemy before undertaking more serious operations in northern Syria . Consequently , the Muslim army marched to Emesa with Khalid ' s mobile guard in the lead . On arrival at the city , a short battle was fought between Khalid ibn Walid ' s mobile guard and the Byzantine garrison of Emesa . The Muslims drove the Byzantine guard back , which forced the Byzantines to withdraw into the fort and close the gates . Abu Ubaidah ibn al - Jarrah arrived with the rest of the army and deployed it into four groups opposite the four gates of Emesa : Emesa was a fortified circular - shaped city with a diameter of less than a mile , and it was surrounded by a moat . There was also a citadel atop a hillock inside the fort . Outside the city stretched a fertile plain , broken only on the west by the Orontes River . Abu Ubaidah himself , together with Khalid and his mobile guard , camped on the north side , a short distance from the Rastan Gate . Abu Ubaidah left the siege in the hands of Khalid , who thus acted as the virtual commander of the Muslims for this operation . It was now late November or early December , and the winter was at its peak . The siege continued and every day there was an exchange of archery , but no major action took place which could lead to a decision either way . The Byzantine expectations that the Muslims would not be able to withstand the cold of Emesa proved to be correct to some extent , but not as they imagined . It was about the middle of March 636 when the worst of the winter was over , that Harbees decided to make a surprise sally and defeat the Muslims in battle outside the fort , as the Byzantine hope of the cold driving the Muslims away vanished . Supplies were running low , and with the coming of spring and better weather the Muslims would receive further reinforcements and would then be in an even stronger position . Early one morning the Rastan Gate was flung open and Harbees led 5 , 000 men into a quick attack on the unsuspecting Muslim army facing that gate . The speed and violence of the attack took the Muslims by surprise , and although this was the largest of the four groups positioned at the four gates , it was driven back from the position where it had hastily formed up for battle . A short distance back the Muslims reformed their front and held the attack of the Byzantines , but the pressure became increasingly heavy and the danger of a break - through became clearly evident . Abu Ubaidah sent Khalid ibn Walid to restore the situation . Khalid moved forward with the mobile guard , took the hard pressed Muslims under his command and redisposed the Muslim army for battle . After all these defensive measures Khalid took the offensive and steadily pushed the Romans back , though it was not till near sunset that the Romans were finally driven back into the fort . The sally had proved unsuccessful . Conquest of Emesa . The following morning Abu Ubaidah held a council of war and expressed his dissatisfaction with the manner in which the Muslims had given way before the Roman attack , whereupon Khalid remarked , " These Romans were the bravest I had ever met . " Abu Ubaidah asked Khalid for his advice and Khalid told him his plan . The next morning they would make a fake withdrawal of the army from Emesa giving the Byzantines the impression that the Muslims were raising the siege and were withdrawing to the south . The Byzantines would surely attack the rearguard of the withdrawing Muslim army and at that moment the army would turn back , encircle the Byzantine army and annihilate them . According to the plan , early the following morning , the Muslims raised the siege and withdrew to the south . Viewing it as a brilliant military opportunity , Harbees immediately collected 5 , 000 Byzantine warriors and led them out of the fort to chase the Muslims . He launched his mounted force into a fast pursuit to catch up with the retreating Muslim forces and strike them down as they fled . The Byzantine army caught up with the Muslims a few miles from Emesa . The leading elements of Byzantine cavalry were about to pounce upon the ' retreating Muslims ' , when the Muslims suddenly turned and struck at the Byzantines with ferocity . As the Muslims turned on the Byzantines , Khalid shouted a command at which two mounted groups detached themselves from the Muslim army , galloped round the flanks of the surprised Byzantines and charged from the rear . Steadily and systematically the Muslims closed in from all sides . It is said that Khalid with a small group of elite mounted warriors of mobile guard reached the centre of the Byzantines army and there he saw Harbees still fighting . Khalid made for Harbees , but was intercepted by a giant Byzantines general , who was killed by Khalid after a duel . At the time when the Muslims started their attack on the encircled Romans , a group of 500 horsemen under Ma ' az ibn Jabal had galloped back to Emesa to see to it that no escaping Roman got into the fort . As these horsemen neared Emesa , the terrified inhabitants and the remnants of the Roman garrison which had not joined the pursuit hastily withdrew into the fort and closed the gates . Ma ' az deployed his men in front of the gates to prevent the Byzantines in Emesa from coming out and the Byzantines outside Emesa from getting in . It is recorded that only about a hundred Byzantines got away . The Muslims , on the other hand , lost about 235 dead in the entire operation against Emesa , from the beginning of the siege to the end of the last action . As soon as this action was over the Muslims returned to Emesa and resumed the siege . The local inhabitants offered to surrender on terms , and Abu Ubaidah accepted the offer . This happened around the middle of March , 636 . The inhabitants paid the Jizya at the rate of one dinar per man , and peace returned to Emesa . Aftermath . Soon after the surrender of Emesa , the Muslims set out once again for the north , intending to take the whole of Northern Syria this time , including Aleppo and Antioch . They went past Hama and arrived at Shaizar . Here a Roman convoy taking provisions to Qinnasrin and escorted by a small body of soldiers was intercepted and captured by Khalid . The prisoners were interrogated , and they provided the information regarding the plan of Heraclius , and concentration of a large Byzantine army at Antioch . The Byzantine army met the Muslims in August 636 on the plain of Yarmuk where the Muslims won a decisive victory against the Byzantines in the Battle of Yarmuk .