During the Second Constitutional period (1908-1918), the most pressing political debate among Ottoman subjects concerned imperial organization. The Committee of Union Progress (CUP) favored centralization, whereas the liberal opposition advocated decentralization along ethnic, religious or regional lines. While Istanbul intellectuals and politicians fought over the empire’s administrative organization, powerbrokers across the Arabian Peninsula—from Yemen to Kuwait—negotiated or tried to negotiate autonomy within an Ottoman imperial framework. Despite the CUP’s anti-autonomy polices, the government was compelled to accept autonomy or offered autonomy preemptively. For example, British Foreign Office officials fought bitterly over the status of Kuwait with ?brahim Hakk? Pa?a—the former Grand Vizier and one of the principal international law experts in the empire. Hakk? Pa?a was compelled to recognize Kuwait as an autonomous kaza in the Anglo-Ottoman Convention of 1913. The legal instrument was a confusing amalgam of elements drawn from earlier Ottoman autonomy schemes and British ideas about “suzerainty” in the princely states and the Gulf shaikhdoms. The Foreign Office and the ?brahim Hakk? differed on the meaning of “suzerainty” and “sovereignty” and so abandoned both words in the Convention. Mubarak al-Sabah was confirmed as the ruler of Kuwait but was also the Kaymakam responsible to the Ottoman government. He was given many of the privileges bestowed upon the family of Mehmet Ali’s family in Egypt—including “complete administrative autonomy” and the central state agreed to abstain from interfering in his domains. This paper is a comparative analysis of the legal status of Ottoman autonomous provinces, the Gulf shaikhdoms and the Indian princely states. While the Ottoman Empire had long maintained flexible administrative arrangements throughout the empire, starting in the 1830s, the exigencies of the Eastern Question resulted in the creation of a new type of province. Categorized as “exceptional” by the Ottoman state, the new autonomous provinces (eyalet-i mümtaze) were the product of an uneasy compromise between the Ottoman and European empires. I argue that these provinces were the key arena in which new possibilities for sovereignty and imperial control were negotiated and tested in the Middle East. Ottoman autonomous provinces, like the Gulf shaikhdoms and the Indian princely states, possessed elements of local control but there were critical differences between them. Ultimately, these experiments in sovereignty and imperial control informed Ottoman and British visions for the post-war order in the Middle East.