Commander in Syria

Abu Bakr sent Abu 'Ubaydah to Syria as one of the army commanders, and he was among the leaders at Yarmuk in 15 AH. When 'Umar became caliph, he made him commander of the Syrian front. In the same period, 'Umar relieved Khalid ibn al-Walid of the command of the army there. Abu 'Ubaydah received 'Umar's letter and did not tell Khalid for a time, wanting to spare his feelings.

Under his command, Damascus, Homs and other towns were taken, and when the people of Jerusalem asked for a treaty they asked that the caliph himself come. 'Umar travelled to Syria, and Abu 'Ubaydah welcomed him.

A well-known report says that when 'Umar visited Abu 'Ubaydah's house he found nothing in it but a sword, a shield and a saddle. 'Umar wept and said that this world had changed all of them except Abu 'Ubaydah.