This essay parts with the compartmentalized way in which scholarship tends to view Iran’s military predicament in the Safavid era by examining the perennial threat the Ottomans posed to the country largely in isolation from the recurring conflict between the Safavids and their other main adversaries, the Mughals and Uzbeks, respectively. The security dilemma facing Safavid Iran, it is argued here, was acute as well as multifaceted, and should be approached as such. All three of its direct neighbors were Sunni and two, the Ottomans and the Mughals, were capable of mobilizing far greater military resources than Iran. The main strategic concern of the Safavids was to prevent these neighbors from joining forces and engaging them in a two-front war. This study examines balancing the strategies employed by the three most consequential Safavid shahs, Esma‘il I (1501‒24), Tahmasb (1524‒76), and ‘Abbas I (1587‒1629), to avoid becoming the target of a simultaneous or combined assault by their neighbors. This analysis provides the backdrop to the rational decision the Safavids made in 1639—to end the threat of a two-front war by concluding a lasting peace accord with their most formidable enemies, the Ottomans.