President Trump keeps looking for the magic formula that will deliver him victory in Iran.

First was the airstrike last June intended, he said, to “obliterate” Iran’s nuclear program. Then came the intense February air campaign carried out with Israel and designed, he said, to deliver regime change and a popular uprising. Then he bet on a blockade of Iranian shipping to end the Iranian stranglehold on the Strait of Hormuz.

Now, in a new effort to break Iran’s control over the strait, Mr. Trump has announced a plan with few details to help guide stranded ships out through it. Iran responded on Tuesday with missiles and drones, and given the risks, most tankers are unlikely to dare crossing the strait for now.

But Mr. Trump’s conviction that these tactics will bring about Iran’s capitulation is deeply flawed, officials and analysts say. They say it is a misreading of the Islamic Republic’s strategy, psychology and capability for adaptation. The Iranian government believes that it has the upper hand for now, and that it can withstand economic pressure, as it has in the past, longer than Mr. Trump can tolerate rising energy prices brought about by the halting of traffic through the strait.

If anything, Iran’s positions have hardened. But Mr. Trump’s tactics have not changed.

“At every point when pressure has not delivered the intended result, he’s sought a new tool of coercion which he believed would magically conjure victory,” said Ali Vaez, Iran project director for the International Crisis Group. “He always believes he’s one little turn of the screw away.”

Pressure can work over time, “but pressure without an open door is an exercise in futility,” Mr. Vaez said. “Trump doesn’t understand that no matter the pressure, so long as you don’t give them a face-saving way out and a mutually beneficial agreement — not capitulation or surrender — you won’t get a deal.”