Invasion of Eastern Roman (Byzantine) Empire
Further information: Muslim conquest of Syria
With a successful invasion of Sassanid Persian province of Iraq, Abu Bakr’s confidence grew. He concentrated four large corps at Zhu Qissah and sent them to Roman Syria. Each corps was assigned its own commander and its own target. The leaders of the different corps received intelligence of a concentration of large Byzantine armies at Ajnadayn while on the march. The army stopped its advance and the leaders wrote to Abu Bakr for help. Since the Muslim position in Iraq was stable by now, the Caliph accordingly wrote to Khalid to take half of his forces of Iraq to Syria and to assume command of all Muslim armies in Byzantine Syria. The Byzantine province of Syria in those days consisted of modern day Syria, Jordan, Israel, the Palestinian territories, Lebanon and southern Turkey. There were two routes towards Syria from Iraq, one was via Daumat-ul-Jandal and the other was through Mesopotamia passing though Ar Raqqah. Since it was believed that the Muslim armies in Syria were in need of urgent reinforcement, Khalid avoided the conventional route to Syria via Daumat ul Jandal because it was a long route and would take weeks to reach Syria. He also did not take the Mesopotamian route because Roman garrisons held northern Syria and northern Mesopotamia. A conflict with these Roman forces would have forced Khalid to spend too much time while Muslim armies were being outflanked in Syria. Khalid selected, instead, a short and unconventional route to Syria, passing though the Syrian Desert. Although probably hyperbole, some sources state that his soldiers marched for two days without a single drop of water before reaching an oasis that Khalid had selected in advance. Khalid thus entered Northern Syria at a point where he was least expected, catching the Byzantine forces on their right flank. More recent historians have suggested that this surprises attack unhinged the Byzantine defenses in Syria.Khalid entered Syria in June 634 and quickly captured the border forts of
Sawa, Arak, Tadmur, Sukhnah. Qaryatayn and Hawarin after the battles of Qaryatayn and Hawarin. After dealing with all these cities, Khalid moved towards Damascus, passing though a mountain pass which is now known as Sanita-al-Uqab (Uqab pass) after the name of Khalid's army standard. From here he moved away from Damascus, towards Bosra, the capital of Ghassanid Arab kingdom, a vassal of Eastern Roman empire. He had ordered other Muslim commanders to concentrate their armies at Bosra, which were still near the Syrian-Arabia border. At Maraj-al-Rahab, Khalid defeated a Ghassanid army of Christian Arabs in a quick Battle of Marj-al-Rahit. Meanwhile Abu Ubaida ibn al-Jarrah, the supreme commander of Muslim armies in Syria had ordered Shurhabil ibn Hasana to attack Bosra.The later laid siege of Bosra with his small army of 4000 men. Roman and Ghassanid Arab garrison, noticing that this might be the advance guard of the larger Muslim army to come, decided to attack and destroy Shurhabil’s army. They came out of the fortified city and attacked Shurhabil, surrounding him from all sides; Khalid reached the arena with his advance guard cavalry and saved the day for Shurhabil. The combined forces of Khalid, Shurhabil and Abu Ubaidah then laid the siege of Bosra, which surrendered some time in mid July 634. thus effectively ending the Ghassanid Dynasty.
Here Khalid took over the command of Muslim armies in Syria from Abu Ubaidah, as per the instructions of Caliph. The massive Byzantine armies were concentrating at Ajnadayn to push the invading armies back to desert. Early Muslim sources have mentioned its size to be 90,000, while most of the modern historians doubt the figures, but consider this battle to be the key to breaking the Byzantine power in Syria. According to the instructions of Khalid all Muslim corps concentrated at Ajnadayn, where they fought a decisive battle against Byzantine on 30 July 634. Defeat at the Battle of Ajnadayn, left Syria vulnerable to the Muslim invaders. Khalid decided to capture Damascus, the Byzantine stronghold. At Damascus Thomas, son in law of Emperor Heraculis, was in charge. Receiving the intelligence of Khalid's march towards Damascus he prepared for the defences of Damascus. He wrote to Emperor Heraculis for reinforcement, who was at Emesa that time. Moreover Thomas, in order to get more time for preparation of a siege, sent the armies to delay or if possible halt Khalid's march to Damascus, one such army was defeated at Battle of Yaqusa in mid-August 634 near Lake Tiberias 90 miles from Damascus, another army that halted the Muslim advance to Damascus was defeated in Battle of Maraj as Saffer on 19 August 634. These engagements delayed Khalid’s advance and gave Thomas enough time to prepare for siege. Meanwhile Heraculis's reinforcement had reached the city, which he had dispatched after the bad news of Ajnadyn. Before Heraculis's another regiment could reach Damascus, Khalid had finally reached Damascus. Khalid reached Damascus on 20 August and besieged the city. To isolate the city from rest of the region, Khalid placed the detachments south on the road to Palestine and in north at Damascus-Emesa route, and several other smaller detachments on routes towards Damascus. Heraculis's reinforcement was intercepted and routed at the Battle of Sanita-al-Uqab, 20 miles from Damascus. Khalid's forces withstood three Roman sallies that tried to break the siege. Khalid finally attacked and conquered Damascus on 18 September 634 after a 30-day siege. According to some sources the siege lasted for four or six months. Heraculis, having received the news of the fall of Damascus, left for Antioch from Emesa. The citizens were given peace on the terms of annual tribute; the Byzantine army was given a three-day peace to go as far as they could. After the three-day deadline was over, the Muslim cavalry under Khalid's command attacked the Roman army, catching up to them using an unknown shortcut, at the Battle of Maraj-al-Debaj, 190 miles north of Damascus. Abu Bakr died during the siege of Damascus and Umar became the new Caliph. He dismissed his cousin Khalid ibn al-Walid from the command and appointed Abu Ubaidah ibn al-Jarrah the new commander in chief of Islamic army in Syria. Abu Ubaidah got the letter of his appointment and Khalid's disposal during the siege, but he delayed the announcement until the city was conquered.