With the 1911 Italian invasion of Tripolitania, Istanbul’s last footing in North Africa came under threat. Outclassed and seemingly outmaneuvered by their Italian opponent, the Ottoman resistance was compelled to rely almost entirely on North African volunteers to fill the ranks of its makeshift army. This paper demonstrates how the exigencies of fighting an asymmetric war in Tripolitania inflected the ideological commitments of Ottoman elites and informed an emerging anticolonial strategy to defend the empire. Recent interpretations of the final wars of the Ottoman Empire (1911-1923) as one unremitting conflict—a “Long First World War”—provide a fruitful framework to understand the development and implementation of these anticolonial strategies. This paper thus discusses the efficacy of Ottoman asymmetric warfare in North Africa and accentuates the limitations and contradictions inherent in Ottoman anticolonialism. Often the building of anticolonial alliances with local stake holders like the Sanūsī Order of Cyrenaica clashed with simultaneous political efforts to reinforce an Ottoman nationalism among the combatants and inhabitants of the North African provinces. Utilizing seldom explored documents from the Turkish General Staff archives and Turkish Red Crescent archives as well as Italian and German archival sources, this paper follows the Unionist officers, like Mustafa Kemal, Enver Pasha, and Eşref Kuşçubaşı, whose anticolonial zeal harmonized with the sentiments of local recruits eager to fight off the Italian invader, on their incognito expedition into Tripolitania to construct a disciplined volunteer force of irregulars. Ultimately, the securing of anticolonial alliances proved more effective than instilling a lasting sense of Ottoman nationalism in the combatants. Still, thousands of volunteers served under Ottoman officers in an anticolonial offensive against the European menace and, despite the signing of peace in 1912, the war persisted with Ottoman backing until the Mudros Armistice (1918). The surreptitious channels of communication, covert supply lines, and the Teşkîlât-ı Mahsûsa, a secret paramilitary organization, initially developed in the 1911-1912 conflict remained decisive features of a continued Ottoman anticolonial campaign in North Africa over the course of World War I. Moreover, the effectiveness of this anticolonial strategy was not lost on the officers who modeled later insurgent movements on their experiences in Tripolitania. The Italo-Ottoman War became the staging ground for Ottoman anticolonial warfare, a feature of the empire’s strategy and resistance in the Long First World War.