The Islamic Republic of Iran's "Look to the East" strategy over the past two decades has become a central pillar of this country's strategic considerations. The central question of this research is: "How has the implementation of the Look to the East strategy redefined Iran's national security calculus within the West Asian regional system, and what costs and benefits has it entailed for Iran?" The paper's core finding indicates an inherent security paradox in this strategy. On one hand, it has created unparalleled opportunities, and on the other hand, this research argues that the strategy has also generated profound challenges affecting Iran's long-term security stability. In its conclusion, the paper emphasizes that the Look to the East strategy, while a strategic necessity for the survival of the Islamic Republic of Iran in the short term, has, in the long term, turned the region into an arena for great power competition and trapped Iran's security in a zero-sum game. proposal is the necessity of moving from an "ideological Look to the East" towards a "pragmatic, cost-benefit-based Eastern strategy," in which a smart balance is struck between short-term and long-term economic-security interests.