The present article is a study of Ottoman military recruitment attempts of Circassians in the northwestern Caucasus. It examines the process of realizing a Circassian highlander army and the administration of the Anapa fortress during the time of two different fortress commanders. Focusing on the deeds of these two pashas regarding Circassian recruitment and their social background, this study highlights the Ottoman-Circassian relations and the dynamics of loyalty and pragmatism. Specifically, the role of provincial networks in ruling the border fortresses and regional politics in the Eastern Black Sea have been underlined within the context of the Russian-Ottoman rivalry over the Caucasus. Rebutting the importance of the origins of Ottoman officers for Ottoman borderland politics, this study argues that the contribution of provincial notables to the Ottoman civilizing mission and the Circassian army project in the early nineteenth century has been indispensable to the realization of Ottoman establishment in the Caucasus.