The killing in October underscores the complex political and security landscape as the United States begins working with interim Syrian President Ahmad al-Sharaa in the fight against remnants of IS. According to relatives, Khaled al-Masoud had been spying on IS for years on behalf of the insurgents led by al-Sharaa and then for al-Sharaa’s interim government, established after the fall of former President Bashar Assad a year ago. Al-Sharaa’s insurgents were mainly Islamists, some connected to al-Qaida, but enemies of IS who often clashed with it over the past decade. Neither U.S. nor Syrian government officials have commented on al-Masoud’s death, an indication that neither side wants the incident to derail improving ties. Weeks after the Oct. 19 raid, al-Sharaa visited Washington and announced Syria would join the global coalition against IS. Still, al-Masoud’s death could be “quite a setback” for efforts to combat IS, said Wassim Nasr, a senior research fellow with the Soufan Center, a New York-based think tank focused on security issues. Al-Masoud had been infiltrating IS in the southern deserts of Syria known as the Badiya, one of the places where remnants of the extremist group have remained active, Nasr said. The raid targeting him was a result of “the lack of coordination between the coalition and Damascus,” Nasr said. In the latest sign of the increasing cooperation, the U.S. Central Command said Sunday that American troops and forces from Syria’s Interior Ministry had located and destroyed 15 IS weapons caches in the south.

Confusion around the raid

The raid occurred in Dumayr, a town east of Damascus on the edge of the desert. At around 3 a.m., residents woke to the sound of heavy vehicles and planes. Residents said U.S. troops conducted the raid alongside the Syrian Free Army, a U.S.-trained opposition faction that had fought against Assad. The SFA now officially reports to the Syrian Defense Ministry. Al-Masoud’s cousin, Abdel Kareem Masoud, said he opened his door and saw Humvees with U.S. flags on them. “There was someone on top of one of them who spoke broken Arabic, who pointed a machine gun at us and a green laser light and told us to go back inside,” he said. Khaled al-Masoud’s mother, Sabah al-Sheikh al-Kilani, said the forces then surrounded her son’s house next door, where he was with his wife and five daughters, and banged on the door. Al-Masoud told them that he was with General Security, a force under Syria’s Interior Ministry, but they broke down the door and shot him, al-Kilani said. They took him away, wounded, al-Kilani said. Later, government security officials told the family he had been released but was in the hospital. The family was then called to pick up his body. It was unclear when he had died. “How did he die? We don’t know,” his mother said. “I want the people who took him from his children to be held accountable.”

Faulty intelligence

Al-Masoud’s family believes he was targeted based on faulty intelligence provided by members of the Syrian Free Army. Representatives of the SFA did not respond to requests for comment. Al-Masoud had worked with al-Sharaa’s insurgent group, Hayat Tahrir al-Sham, in its northwestern enclave of Idlib before Assad’s fall, his cousin said. Then he returned to Dumayr and worked with the security services of al-Sharaa’s government. Two Syrian security officials and one political official, who spoke on condition of anonymity because they were not authorized to comment publicly, confirmed that al-Masoud had been working with Syria’s interim government in a security role. Two of the officials said he had worked on combating IS. Initial media reports on the raid said it had captured an IS official. But U.S. Central Command, which typically issues statements when a U.S. operation kills or captures a member of the extremist group in Syria, made no announcement. A U.S. defense official, when asked for more information about the raid and its target and whether it had been coordinated with Syria’s government, said, “We are aware of these reports but do not have any information to provide.” The official spoke on condition of anonymity in order to discuss a sensitive military operation. Representatives of Syria’s defense and interior ministries, and of U.S. envoy to Syria Tom Barrack, declined to comment.

Increased coordination could prevent mistakes

At its peak in 2015, IS controlled a swath of territory across Iraq and Syria half the size of the United Kingdom. It was notorious for its brutality against religious minorities as well as Muslims not adhering to the group’s extreme interpretation of Islam. After years of fighting, the U.S.-led coalition broke the group’s last hold on territory in late 2019. Since then, U.S. troops in Syria have been working to ensure IS does not regain a foothold. The U.S. estimates IS still has about 2,500 members in Syria and Iraq. U.S. Central Command last month said the number of IS attacks there had fallen to 375 for the year so far, compared to 1,038 last year. Fewer than 1,000 U.S. troops are believed to be operating in Syria, carrying out airstrikes and conducting raids against IS cells. They work mainly alongside the Kurdish-led Syrian Democratic Forces in the northeast and the Syrian Free Army in the south.

Now the U.S. has another partner: the security forces of the new Syrian government. Airwars, a London-based conflict monitor, has reported 52 incidents in which civilians were harmed or killed in coalition operations in Syria since 2020. The group classified al-Masoud as a civilian. Airwars director Emily Tripp said the group has seen “multiple instances of what the U.S. call ‘mistakes,’” including a 2023 case in which the U.S. military announced it had killed an al-Qaida leader in a drone strike. The target later turned out to be a civilian farmer. It was unclear if the Oct. 19 raid went wrong due to faulty intelligence or if someone deliberately fed the coalition false information. Nasr said that in the past, feuding groups have sometimes used the coalition to settle scores. “That’s the whole point of having a hotline with Damascus, in order to see who’s who on the ground,” he said.