DUMAYR, Syria -- A raid by U.S. forces and a local Syrian group aiming to capture an Islamic State group official instead killed a man who had been working undercover gathering intelligence on the extremists, family members and Syrian officials have told The Associated Press.

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 o

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