By the summer of 1913, the lands of Macedonia ceased to be a part of the Ottoman Empire. The conquest of the region compelled hundreds of thousands of Muslims to take flight to Anatolia and resulted in the destruction of towns, villages and quarters associated with the region’s Muslim population. These aspects of the end of Ottoman rule in the Balkans are by no means unknown to scholars or the Turkish general public; one may say in fact that Macedonia’s annexation, as well as the departure of so many of region’s Muslims, possesses an Ur resonance within Turkey, constituting a definitive moment in the making of the modern republic and its people. Our contemporary understanding of the end of Ottoman imperium in Macedonia however is admittedly rather one-sided. Current scholarship has been relatively content not to pursue how the empire’s culture and administration was dismantled immediately following the Treaty of London of May 1913. While we are familiar generally with the plight of the region’s Muslim refugees, it remains largely unclear how Macedonia’s remaining inhabitants encountered and negotiated with the end of Ottoman rule. Lastly, it remains to be seen how Istanbul politicians and local Ottoman diplomats perceived Rumeli’s departure during the immediate aftermath of the war. The paper presented below represents an initial study of Macedonia’s political and social transition away Ottoman rule. Focusing on the years between 1912 and 1918, this paper delves into the diplomatic correspondence of British, Austrian, German and Ottoman observers present in the region during the empire’s collapse. The principle subject of this study is the region that came to be known as “Old Serbia” or what is today the lands of the Republic of Macedonia and Kosova. A preliminary survey of these records reveal three particular trends: 1) Macedonian Muslims struggle to stay in their homes and integrate into the emerging Serbian order; 2) the Serb administration of the region wavered between acts of oppression towards both Muslims and Exarchists and deliberate attempts to mobilize Muslim support and maintain the status quo; 3) through the First World War, Ottoman officials continued to monitor and bemoan the plight of Muslims. Continued official interest in Macedonian Muslim affairs tended to reinforce the established narrative of extreme Muslim suffering and exclusion at the expense of emphasizing Muslim acts of collaboration and similar hardships suffered by Greek and Bulgarian Orthodox Christians.