The case of Iran and its involvement in Syria and Iraq provide insight about both the motives of authoritarian promoters and why they choose certain mechanisms to promote autocracy. Similar to other regional authoritarian promoters, the Iranian leadership perceives a strong relationship between the survival of their regime and the persistence of authoritarianism in both Syria and Iraq, demonstrating the interconnectivity between geopolitics, strategic incentives, and the promotion of authoritarianism. Iran’s choice of direct military involvement in Syria is one of the highest and most costly forms of international support for an authoritarian regime in the world today. I argue that the weakness of the Syrian government, combined with the strategic importance of the state, forced Iran to provide direct military assistance to help maintain Syrian President Bashir Assad’s rule. In contrast, although Iran has also provided high levels of political and financial support to the Iraqi regime, they have not engaged in direct military intervention to promote autocracy because Iraqi Shiites have been less dependent on Iran for survival.