Intense international sanctions have heavily compromised Iran’s economy and national security. In response, the Islamic Republic of Iran has formally elevated the "Look East" policy as a cornerstone of its economic and political diplomacy. Employing an analytical-descriptive framework, this study evaluates this approach as a strategic adaptation to sanctions, examining its outcomes in trade and economic security alongside its structural and political challenges over the past two decades. Key strategies analyzed include deepening strategic partnerships with China and Russia (specifically the 25-year agreement), active engagement in Eastern-led regional frameworks like the Shanghai Cooperation Organization (SCO) and the Eurasian Economic Union (EAEU), and diversifying transit corridors toward Asia. Findings indicate that while this strategy has partially mitigated sanctions shocks, cultivated alternative markets, and reduced international isolation, it remains constrained. Major challenges include an asymmetrical power balance favoring Eastern partners, a potentially detrimental dependency on China's economy, reduced diplomatic flexibility from overconcentration on a single front, and limited capital and technology absorption capacity. Consequently, this study contends that while the "Look East" strategy has been a necessary response shifting Iran’s economic geopolitics, its reactive and lopsided nature prevents it from independently ensuring sustainable economic security. Long-term success demands intelligent hedging, enhanced domestic bargaining power, and structural economic reforms to prevent Iran from being relegated to the periphery of an East-centered economic order.