Iran’s Tests of Trump Will Keep Coming, and They’re Going to Get Worse

By Noah Rothman

Friday, June 26, 2026

 

It was Iran’s terrorist cat’s-paws in Hezbollah who were the first to test Trump’s commitment to his supposedly war-ending memorandum of understanding with the Islamic Republic.

 

The remnants of the Iranian regime had telegraphed their understanding that the first clause of the document was designed to constrain Israel’s defensive actions in southern Lebanon. Perhaps Tehran wanted to see if Hezbollah’s aggression would convince Washington to abandon its efforts to tighten the reins on Israel. It didn’t.

 

The whole point of provocations like these in an environment in which neither war nor peace prevails is that they test and, therefore, redefine the parameters in which the enemy can act freely. The next test — and there’s always another test — will attempt to expand those parameters further.

 

And that’s precisely what happened on Thursday.

 

“Iran’s Islamic Revolutionary Guard Corps attacked a Singapore-flagged cargo ship Thursday in the Strait of Hormuz,” the Wall Street Journal reported, in what officials believe was a “deliberate” drone strike on commercial shipping. “The incident took place near the coast of Oman hours after the Iranian paramilitary’s navy warned ships not to use routes through the waterway that the regime hadn’t sanctioned.”

 

This represents a direct Iranian attack not just on America’s erstwhile role as guarantor of free maritime navigation rights, but the MOU itself. That document compels Iran “upon signing” to make “its best efforts” to ensure the “safe passage of commercial vessels with no charge,” albeit “for 60 days only.” It’s certainly a betrayal of the trust America placed in the Islamic Revolutionary Guard Corps — a U.S.-designated terrorist group, the representatives of which have been dispatched to “hang out” with American CENTCOM officials in Doha, according to the vice president.

 

Perhaps the American side of this equation will treat their IRGC counterparts to a gentle scolding in between air hockey matches at the SMP lounge.

 

Trump has reserved for himself the right to enforce the MOU’s terms by force, but his threats are hollow. He issues them regularly but hasn’t acted on any in a way that would convey resolve since Operation Epic Fury ended in early April.

 

When Iran’s provocations did prompt an American kinetic response, it was calibrated and proportionate. The effect of those actions was only to communicate the president’s reluctance to return to war — an impression likely confirmed by Trump’s willingness to halt those strikes mid-sortie at the request of Iran’s duplicitous diplomats.

 

Throughout the two-month cease-fire, the president demonstrated a willingness to endure humiliation after humiliation, all while bombastically warning that his patience was about to come to an end. But it never did. The Iranians are therefore unlikely to believe Trump is serious until and unless the bombs start falling again.

 

Iran wants to make this MOU as painful as possible for the president, maximizing every opportunity to cement the impression that they won and he lost. Why anyone in the president’s circles believes that the Iranians will be quiet enough to allow the GOP to salvage its  political prospects in the midterms is anyone’s guess. That is a delusion fueled by motivated reasoning. And it is a delusion that could be dispelled if the appeasers in Trump’s orbit would internalize one obvious truth: Iran wants Trump and America to lose.

 

Since April 8, Iran’s bayonets have encountered only mush. As the axiom dictates, we can expect that the Islamic Republic will keep pushing.