This May Be Trump’s Biggest Error in the Iran War
The Atlantic · LC · trust 62/100
Success requires knowing what motivates your enemy.
Fatemeh Bahrami / Andalou / Getty July 31, 2026, 8 AM ET Share Save Sign up for our newsletter about national security here .
F or 2,500 years , military commanders have heeded the injunction of Sun Tzu, the great Chinese military strategist: Know your enemy. Yet the Trump administration’s greatest mistake in the Iran war may be its persistent failure to understand Tehran’s priorities and motivations—and how much punishment the regime is willing to absorb to prevail.
Iran’s decision Tuesday to launch ballistic missiles at U.S. troops in Jordan was a prime example. It befuddled Washington. U.S. officials had come to expect that their actions would drive the war, and Iran would react. But here was Tehran, escalating matters just after the United States had suspended its 13-day barrage of strikes against Iranian defenses and infrastructure. U.S. Central Command, which is responsible for military operations in the Middle East, described the move as a “surprise attack.”
Tehran characterized the missile strikes as self-defense against what the regime saw as the Trump administration’s broadening of the war. Around the same time as the Iranian attack, U.S. and Saudi forces launched joint strikes on Iran-backed militias in Iraq, Riyadh’s first publicly acknowledged military strikes of the conflict. Turki al-Maliki, a Saudi defense-ministry spokesperson, said in a statement that the militias had attacked the kingdom’s oil facilities and that Riyadh reserved the right to respond “at the appropriate time and place.”
This week’s events hardly represented the first time that the two sides had misread each other’s intentions. The convoluted and complicated war has swung almost weekly between peace overtures and fighting. Those misinterpretations appear set to continue, especially amid signs that others may be dragged into the fight. Egyptian officials earlier this week confirmed that a drone had set two gas vessels ablaze at Damietta, a port city on the Mediterranean near the Suez Canal. No group has claimed responsibility, but the attack raised fears that Iran has expanded its list of nations to target.
T he memorandum of understanding that Washington and Tehran signed in the middle of last month quickly devolved into one of the war’s signature misunderstandings . The very first clause of the agreement promised to end the fighting, but the two sides had fundamentally different interpretations of their obligations.
The memorandum did not end the dispute over the Strait of Hormuz but rather, it papered over it. Washington believed it had secured 60 days of open, toll-free commercial navigation. Tehran read the agreement as preserving its authority to manage traffic through the waterway. As the dispute erupted, some Iranian officials believed that the U.S. had purposely drafted a vague agreement to trigger a violation that could be used as a predicate to resume strikes, a person familiar with their thinking told us. And the U.S. sought to use financial incentives, such as sanctions waivers and investment, to entice a government that was preoccupied with the assassination of its supreme leader. Was anyone really surprised that the pact fell apart? Certainly not President Trump, who professed that he “couldn’t care less” after each side had walked away.
Even before the war began, in late February, the two governments were talking past each other. The U.S. believed that Iran was fragile and the regime susceptible to collapse after nationwide protests . The regime believed that nothing short of its total capitulation to U.S. demands would prevent a war. Trump ordered the war to begin while talks were still under way, and his administration believed that the death of Iran’s supreme leader, Ayatollah Ali Khamenei, on the conflict’s first day would quickly be followed by the collapse of the state. Instead, five months in, the regime remains intact and seems to have enough confidence to endure any U.S. response.
This could put the two sides on a path to escalation, each remaining convinced that more military pressure will force the other to abandon its objectives. “America’s calculation is that escalation would lead to surrender. Iran’s calculation is that escalation would lead to deterrence,” Vali Nasr, a professor of international affairs and Middle East studies at the Johns Hopkins School of Advanced International Studies, told us.
Trump promised on Fox News earlier this week to “beat the fucking shit out of them.” Iran’s Islamic Revolutionary Guard Corps, meanwhile, said that the base in Jordan would remain a target because “as long as threats against Iran persist, resistance will persist.” (The Jordanian military said that all five missiles fired Tuesday were intercepted.) But neither side seems able to answer the question that matters most: What if escalation doesn’t work?
Escalation is “a means to an end, but we don’t know what the end is,” Danny Citrinowicz, a former Israeli intelligence officer who specializes in Iran, told us.
P art of the confusion may stem from the fact that Trump himself appears to be of (at least) two minds about how he wants to proceed. He has vacillated between backing more military action and giving peace talks a chance. The U.S. cannot begin to understand its enemy if it has yet to settle on its own aims—or how to achieve them. Trump has repeatedly sought to back away from the conflict, but during a meeting with senior advisers last Friday, he seriously considered ramping up attacks. He opted not to, but the plans remain on his desk, a senior White House official told us. A pause in U.S. strikes that began Saturday was over by midweek following Iran’s attack on the base in Jordan.
The U.S. is seeking to understand an enemy that is changing and adapting. Iran appears intent on reintroducing the element of military surprise, driven by the belief that it can outlast Trump and that negotiations no longer present a…
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