Despite receiving limited attention in historical literature, military relations between Iran and Italy during the Pahlavi era were marked by significant strategic and multifaceted dimensions. This article, based on unpublished archival documents, explores the evolution of these relations in two main phases. The first phase (1930s–1940s) was characterized by military training cooperation, the dispatch of Iranian naval officers to Italy, and the overhaul of Iranian naval destroyers. In the second phase (1960s–1970s), cooperation expanded considerably to include specialized training, arms contracts, technology transfer, and participation in the establishment of Iran’s military-industrial infrastructure. Employing a descriptive-analytical approach and drawing on Iranian and non-Iranian archival sources and library materials, the article demonstrates that Iran—pursuing a strategy of diversifying its military suppliers—regarded Italy as a non-hostile partner without a colonial legacy. Meanwhile, Italy sought to solidify its foothold in Iran's lucrative arms market. These collaborations were forged within a framework of mutual interests, the anti-communist discourse of the Cold War, and the Shah’s personal commitment to military modernization. Findings suggest that Iran utilized Italy’s industrial and technological capacities to strengthen its armed forces and reduce dependence on major powers, while Italy, recognizing Iran's geostrategic significance, viewed the country as both a vital arms market and a strategic military-industrial partner. Ultimately, this relationship evolved into a model of military diplomacy between a regional power and a mid-ranking European industrial state.