States often build alliances with non-state actors to address their security needs and pursue their strategic objectives, but such alliances are highly unreliable and fraught with grave risks for the allying parties. The gradually increasing capabilities of a non-state actor may embolden it to give preferences to its own geopolitical agenda, thereby adversely affecting the alliance. Thus, states and non-state actors have mostly failed to maintain stable relationships due to diverging interests and opportunistic politics. Iran and Hezbollah have however maintained an alliance, which has entered its fourth decade of organisational existence, and this potentially hostile alliance is transforming the regional strategic landscape. The longevity of their alliance is somewhat puzzling. This article contends that the Iran-Hezbollah alliance has withstood collapse because Iran gives significant autonomy to Hezbollah, and Hezbollah controls and optimizes its resources and revenue which are at its disposal. Additionally, the chaotic regional structure and their intersecting interests play a pivotal role, not only fostering this nexus but also significantly potentiating the survival of their alliance while reducing the likelihood of opportunistic dissociation.