This paper examines the Ottoman surrender of Medina to the leaders of the British-backed Arab Revolt, the Hashemites, in light of the waning confidence in their claim to be true Arab leaders to take the city at the start of the Arab Revolt in June 1916. With the signing of the Mudros Armistice on October 30, 1918, all hostilities with the Ottoman empire ceased and forces were called to surrender; however, a rogue Ottoman commander in Medina refused to give up the city until January 13, 1919. Those months negotiating the surrender of the city were more than just a curious episode in the history of the Middle East theatre. They revealed an underlying anxiety for the Hashemites, whose claim to authority in the Arab world rested in part on their descent from the Prophet Muhammad, who was entombed in Medina. The Hashemites had tried numerous times to take the holy city since the start of the Arab Revolt in June 1916 but failed to claim it despite making gains northward in Aqaba and in Syria. This inability ultimately represented a constant vulnerability for the Hashemites whose leader, Husayn ibn ‘Ali, had crowned himself King of the Arabs in October 1916. By tracing the arc of criticisms for the Hashemites in regards to Medina--how their rivals, Ottoman, Arab, and European, discussed their failure to take the city to how the resulting looting and pillaging that marked their entrance was discussed among Arab and Muslim circles--this paper challenges narratives and timelines that considered the end of the Arab Revolt to October 1918 with the triumphant entrances of Arab forces into Damascus and Aleppo. By focusing on events in the Hijaz at the end of World War I, this paper examines how the Hashemite project had already faltered before the colonial period that would see the Arab Middle East divided into British and French Mandates and their reputation besmirched by colonial collusion. For the Hashemites, Medina became a failure that besmirched their reputation as Arab leaders and the global protectors of Islam and would haunt them into the colonial period.