ABSTRACT This study examines the formative years of Iran’s so-called ‘jihadi field diplomacy’ toward Azerbaijan during and after the First Nagorno-Karabakh War. To accomplish this, I adopt a novel version of neoclassical realism, which considers the socially constructed nature of variables. The application of constructivist neoclassical realism facilitates a deeper comprehension of the reasons and mechanisms behind Iran’s embrace of unconventional interventionist policies in Azerbaijan. I argue that Iran’s jihadi field diplomacy is characterized by two main features: the use of military tools to achieve foreign policy goals and a distinct leadership structure that operates independently of the government. Then I analyze three turning points that shaped Iran’s jihadi field diplomacy toward Azerbaijan. Firstly, after a failed diplomatic mediation between Yerevan and Baku in May 1992, Iran intensified its military and ideological efforts in Azerbaijan. Secondly, during the June 1993 coup, Iran supported pro-Russian coup leader Colonel Huseynov and sought to persuade him to collaborate with ex-Communist Aliyev against nationalist President Elchibey. Aliyev later perceived this initial cooperation as a serious ideological and military challenge. Lastly, the perceived threat and Iran’s Quds Force connections to the leaders of the subsequent military uprisings adversely affected bilateral relations between Iran and Azerbaijan.