Despite the long-standing proximity between Ottoman and Iranian reformists, the Young Turk policy toward Iran was notably reserved. The numerous tensions between Istanbul and Tehran during the constitutional period are often attributed to Young Turk pragmatism. Conversely, this study emphasizes the cultural factors in Irano-Ottoman relations and their influence on the Ottoman perception of Iran following the Ottoman Revolution of 1908. Drawing on the reports written by Hüseyin Hasib Efendi, Ottoman ambassador in Iran from 1909 to 1913, it argues that the multilayered nature of Ottoman modernity and the anxieties of the late Ottoman bureaucratic elite were crucial in shaping the Porte’s policy toward Iran. The article introduces the concept of entangled Orientalism to describe the process of Ottoman discursive adaptation to the West-dominated international order. Additionally, it aims to reassess the role of the Russian menace in the Ottoman understanding of regional politics.