Two years after withdrawing from the Iran nuclear deal, U.S. President Donald Trump's "maximum pressure" campaign has failed to change Iran's regional behavior, bring Tehran back to the negotiation table, curb its nuclear and missile programs, and counter Iran's proxy influence in the region. Instead, Iran has adopted a "maximum resistance" strategy to deal with Washington's pressure. According to the Neorealist school of thought in International Relations (IR), rising systemic or structural pressure on a given state is expected to alter its policies or even its regime. The case of Iran appears to challenge this expectation. This article suggests that Iran has adopted an "anti-containment" strategy to deal with the U.S. pressure. The strategy is based on asymmetric deterrence, the main pillars of which are employing local allied forces and enhancing air and naval deterrence capabilities. Meanwhile, Iran's military-security establishment has gained the upper hand in dealing with the United States, sidelining the diplomatic apparatus. This situation bears the risk of a confrontation between Iran and the United States while leaving no space for meaningful diplomatic engagement.