After Abu Bakr died in 634, his successor, Umar, was determined to continue the Caliphate's expansion deeper into Syria. Though previous campaigns led by Khalid had been successful, he was replaced by Abu Ubaidah. Having secured southern Palestine, Muslim forces now advanced up the trade route, and Tiberias and Baalbek fell without much struggle and conquered Emesa early in 636. The Muslims then continued their conquest across the Levant.

To check the Arab advance and to recover lost territory, Emperor Heraclius had sent a massive expedition to the Levant in May 636. As the Byzantine army approached, the Arabs tactically withdrew from Syria and regrouped all their forces at the Yarmuk plains close to the Arabian Peninsula, where they were reinforced, and defeated the numerically superior Byzantine army.

The Battle of the Yarmuk is regarded as one of the most decisive battles in military history, and it marked the first great wave of early Muslim conquests after the death of the Islamic prophet Muhammad, heralding the rapid advance of Islam into the then-Christian Levant. The battle is widely regarded to be Khalid ibn al-Walid's greatest military victory and cemented his reputation as one of the greatest tacticians and cavalry commanders in history.