Around 5 p.m. Monday, Israeli warplanes streaked across the Syrian border, striking an embassy building in Damascus and killing a cadre of senior Iranian military commanders with the kind of pinpoint accuracy that has earned Israel’s military fear and respect across the Middle East.

Several hours later, the same Israeli military rained missiles on an aid convoy on a coastal road in the Gaza Strip, a botched operation that left seven foreign aid workers dead and Israel’s reputation in tatters. Its leaders were forced to admit to a string of lethal mistakes and misjudgments.

How one of the world’s best-equipped, best-trained militaries could pull off a dangerous strike on foreign soil and then stumble with such tragic consequences in Gaza raises a raft of hard questions — not least how the Israeli military enforces the rules of engagement in its war against Hamas.

Israeli officials attribute the strike on the aid group, World Central Kitchen, to factors common in war: a complex battlefield, where combatants mix with civilians; reduced visibility because it was nighttime; and a moving target, which gave the commanders only minutes to make decisions.

The Damascus raid was the mirror image: a meticulously planned, precisely timed operation against a stationary target, most likely approved at the highest levels of the Israeli military and government.

Details provided by members of Iran’s own Revolutionary Guard suggest Israel had intelligence up to the minute of the strike, including when the ambassador and other civilians had left the building and that key Iranian commanders were there to meet Palestinian militants to discuss the war in Gaza.

In contrast, military analysts in Israel and the United States said Israel’s explanations do not fully account for what happened along the Gaza coast Monday night. The accidental killing of the aid workers, several said, was the predictable result of a shoot-first style of engagement Israeli troops have used in their military campaign since the Hamas attacks of Oct. 7.

“It was not a question of accuracy because it was highly accurate,” said Yagil Levy, a professor and expert on the Israeli military at the Open University of Israel. “It was not a question of negligence, because the action was taken after close consideration of the circumstances.”

“In Gaza, the IDF is committed to killing as many Hamas fighters as possible,” he continued, using an acronym for the Israeli military. “In many cases, targeting Hamas combatants is at odds with the principle of respecting the immunity of civilians.”

Levy said aid convoys in Hamas-controlled Gaza were often guided by armed locals with ties to the militants to prevent their supplies from being damaged or stolen. For the Israeli military, which uses drones to monitor the convoys, that raises the prospect that some of the passengers constitute legitimate combat targets.

The Israelis struck the World Central Kitchen convoy after it had delivered supplies from a jetty to a warehouse. The three vehicles were traveling back when the Israeli military launched three strikes. Two of the vehicles were destroyed, and a third had a gaping hole in its roof next to the seal that identified it as belonging to World Central Kitchen, the charity founded by chef José Andrés.

Andrés said the military would have known his workers’ locations because it was in communication with them. “This was not just a bad-luck situation where, ‘oops,’ we dropped the bomb in the wrong place,” he said to Reuters.

“It was a mistake that followed a misidentification, at night during the war in a very complex condition,” the Israeli military chief of staff, Lt. Gen. Herzi Halevi, said Tuesday. Prime Minister Benjamin Netanyahu vowed, “We will do everything so that this thing does not happen again.”

Some likened the episode to an errant U.S. drone strike in Afghanistan in 2022 that killed 10 innocent people, including seven children. As in Gaza, that strike was based on aerial video imagery. It came after a suicide bombing killed at least 182 people, including 13 U.S. troops, during the frantic U.S. withdrawal from the country.

Under acute pressure to avert another attack, the U.S. military believed it was tracking a terrorist who might imminently detonate another bomb. Instead, it killed an Afghan aid worker and nine members of his family.

“We had just lost troops to a bomb, and there was fear of another bomb,” said John Nagl, a professor of war-fighting studies at the U.S. Army War College in Carlisle, Pennsylvania. “The Israelis felt their troops were in danger. The desire to protect the troops overrode the decision to protect civilians.”

By contrast, Nagl said, the strike on the embassy in Damascus was “flawlessly executed.” The Israelis, he said, “controlled the time and place of the action, and it was on a fixed site. The hard part of that mission was the intelligence gathering, not the military operation.”

Israel still faces international repercussions from the strike, which inflicted serious damage on Iran’s Quds Force, the external military and intelligence service of the Revolutionary Guard. Syria and Iran both expressed outrage, while U.S. officials voiced fears that it could prompt retaliatory strikes against Israel or its ally, the United States.

The botched raid in Gaza, however, has brought a global wave of opprobrium on Israel, which was already becoming more diplomatically isolated. In Britain, the family of one of the killed aid workers, John Chapman, said in a statement, “He died trying to help people and was subject to an inhumane act.”

This is not the first time Israeli soldiers have accidentally hit civilians. In December, they mistakenly shot dead three Israeli hostages in Gaza City, causing outrage in Israel. In January, an Israeli tank opened fire on a convoy for Paltel, the largest telecommunications company in Gaza, killing two technicians, according to the company. The Israeli army said it was investigating the incident but has not announced any conclusions.

Those accidents only add to the pressure facing Israel in light of the spiraling death toll in Gaza. According to health officials in the Hamas-controlled enclave, more than 32,000 people have been killed in six months of war, many of them children. The Gaza Health Ministry’s tally includes both civilians and combatants.

Nagl said he believed the Israeli military should tighten its rules of engagement — the conditions under which soldiers are permitted to open fire — particularly because the number of Hamas fighters in the civilian population had declined since the fighting began in October. Israeli experts said the Israeli military should learn how to better identify targets.

“Tens of thousands of targets have been successfully identified,” said Michael B. Oren, a former Israeli ambassador to the United States who once served as a spokesperson for the Israeli military. “The WCK workers, tragically, weren’t. The IDF will investigate, conclude how and why the error occurred and draw lessons that will help prevent similar errors in the future.”

But Oren and other Israelis pushed back on the suggestion that the Damascus raid was a useful comparison.

“Outside of Gaza — in Syria, for example — Israel faces far fewer complexities,” he said. “Targets are much more easily identified and eliminated, with far less scope for human error.”

Maj. Gen. Tamir Hayman, the former Israeli military intelligence chief, characterized a special operation like that in Damascus as “the kingdom of certainty.” By contrast, he said, “a war is the kingdom of uncertainty.”

The targeted strike in Syria, Hayman said, was like a hunter “pursuing a single animal in the desert.” Fighting in Gaza was like stalking an adversary in a “jungle.” “In one place,” he said, “the chance of making a mistake is low, and in the other, it’s high.”

Uzi Arad, a former national security adviser to Netanyahu who is now a critic, also rejected the comparison, saying the “sheer intensity” of the fighting in Gaza had even led Israeli soldiers to open fire on each other. “Mistakes happen,” he said. “The situation is changing all the time; it’s not static. It’s very dynamic.”

Arad, who is also a former official in Mossad, Israel’s foreign intelligence service, said everything should be done to prevent such errors, but he suggested that they were inescapable on a battlefield like Gaza.

Amos Harel, a military affairs columnist for the Israeli paper Haaretz, acknowledged the challenges of fighting a war in Gaza, but he said the deadly strikes on the convoy were also simply a result of attrition.

“After fighting for such a long time, you get more of these mistakes and problems,” Harel said. “It’s not justified in any way, but it’s the price of ongoing war under these extreme circumstances.”

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