ABSTRACT Through historical analysis and literature review, the current article compares the works of two contemporaneous leading Muslim advocates of reform: Abd al-Rahman al-Kawakibi and Ayatollah Muhammad Husain Naini. The comparison is confined to the primary political treatises of the authors, namely Tabaiʿ al-ʾIstibdad wa-Masariʿ al-ʾIstiʿbad and Tanbih al-Ummah va Tanzih al-Milla. The article delves into the multifaced factors that shaped both the style and content of the two works. Al-Kawakibi and Naini hailed from different Middle Eastern countries, belonged to distinct Islamic schools and occupied varying social strata. These differences have influenced the ways in which they conceptualized the relationship between Islam and political reform. Furthermore, despite their shared diagnosis of tyranny as a malady afflicting Islamic societies, the two authors have prescribed divergent remedies. Consequently, these two works represent the culmination of two discrete approaches to reform, rendering them not merely distinct, but in certain aspects, diametrically opposed.