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For decades, Israel and Iran have fought a shadow war across the Middle East, trading attacks by land, sea, air and in cyberspace.

Iran has largely used foreign proxies to strike Israeli interests, while targeted assassinations of Iranian military leaders and nuclear scientists have been a key part of Israel’s strategy.

Israel’s strike in the Syrian capital, Damascus, that killed three top Iranian commanders on Monday was the most brazen attack in years, raising fears of a wider confrontation. That would be particularly dangerous in a region already in turmoil on multiple fronts, including Israel’s war in Gaza, cross-border skirmishes between Israel and the Lebanese militant group Hezbollah and attacks by Yemen’s Houthi militia against Western interests in the Red Sea. An escalation between Israel and Iran would also risk further entangling the United States, given the presence of American troops in the region.

Here are some key moments in the yearslong conflict.

The assassination of Maj. Gen. Qassim Suleimani, commander of the foreign-facing arm of Iran’s Islamic Revolutionary Guards Corps, in an American drone strike in Baghdad was greeted with satisfaction in Israel.

Iran hit back by attacking two bases in Iraq that housed American troops with a barrage of missiles, injuring about 100 U.S. military personnel.

American officials accused General Suleimani of causing the deaths of hundreds of soldiers during the Iraq war. They also said that he was behind destabilizing Iranian activities throughout the Middle East and that he was accused of plotting attacks against U.S. embassies and Israeli targets.

The general had built a network of allied militias to defend Iran’s interests across the Middle East and to counter the United States and Israel.

Iran and Israel reportedly carried out a number of covert attacks and counterattacks in the years following General Suleimani’s death.

Israel killed Iran’s top nuclear scientist, Mohsen Fakhrizadeh, in November 2021, and followed up with the assassination of a Revolutionary Guards commander, Col. Sayad Khodayee, in May 2022.

In July 2021, an oil tanker managed by an Israeli-owned shipping company was attacked off the coast of Oman, killing two crew members, according to the company and three Israeli officials.

Two of the officials said that the attack appeared to have been carried out by several Iranian drones that crashed into living quarters underneath the ship’s bridge. Iran did not explicitly claim or deny responsibility, but a state-owned TV channel described the attack on the ship as a response to an Israeli strike in Syria.

Once Israel’s bombardment of Gaza began after the Hamas-led attacks on Oct. 7, Iranian-backed militias stepped up their attacks.

At the end of last year, Iran accused Israel of killing a high-level military figure, Brig. Gen. Sayyed Razi Mousavi, in a missile strike outside Damascus. A senior adviser to the Revolutionary Guards, General Mousavi was described as having been a close associate of General Suleimani and was said to have helped oversee the shipment of arms to Hezbollah.

Israel, adopting its customary stance, declined to comment directly on whether it was behind General Mousavi’s death.

The Pentagon launched a drone strike in Baghdad that killed a senior figure in an Iran-linked militant group.

The attack came days after an explosion in a suburb of Beirut, Lebanon, that killed Saleh al-Arouri, a Hamas leader, along with two commanders from that group’s armed wing. The blast was the first such assassination of a top Hamas official outside the West Bank and Gaza in recent years.

Officials from Hamas, Lebanon and the United States ascribed the attack to Israel, which did not publicly confirm involvement.

Mr. al-Arouri was the most senior Hamas figure to be killed since Israel vowed to destroy the organization after Oct. 7.

Israel was blamed for a number of attacks in Syria and Lebanon. In February, Syrian state news media said Israel was behind an airstrike on a residential building in Damascus that killed two people.

The Israeli military declined to comment on that strike, though it has acknowledged hundreds of past strikes on Iran-linked targets in Syria.

But the Israeli military did acknowledge a strike in southern Lebanon in February that it said killed a Hezbollah commander, and in March, it killed a senior Hamas operative in an airstrike also in southern Lebanon.

An Israeli drone strike targeted a car in southern Lebanon, killing at least one person. Israel’s military said it had killed the deputy commander of Hezbollah’s rocket and missile unit. Hezbollah acknowledged the death of a man, Ali Abdulhassan Naim, but did not provide further details.

The same day, airstrikes killed soldiers near Aleppo, northern Syria, in what appeared to be one of the heaviest Israeli attacks in the country in years.

Those strikes killed 36 Syrian soldiers, seven Hezbollah fighters and a Syrian from a pro-Iran militia, according to the Syrian Observatory for Human Rights, a British-based group that tracks Syria’s civil war.

Israel’s military did not claim responsibility. However, the country’s defense minister, Yoav Gallant, wrote on social media, “We will pursue Hezbollah every place it operates and we will expand the pressure and the pace of the attacks.”

Three days later, on Monday evening, Israeli warplanes struck the building in Damascus in the attack that killed the three top Iranian commanders.

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