President Barack Obama’s order for U.S. commandos to target an Islamic State commander in Syria was part of an evolving strategy to disrupt the militant group, which has proven resilient to airstrikes intended to break its grip on parts of the Middle East.

The raid seized on a rare opportunity to act on real-time intelligence. A man the U.S. called Abu Sayyaf — a common nom de guerre in the Arab world — who was identified as a leader of the group’s oil, gas and financial operations was killed, along with about a dozen other militants, with no U.S. casualties, administration officials said.

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