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President Donald Trump dispatched senior officials to meet with Hamas leaders, in a break with a long-standing policy against contacting a group the U.S. considers a terrorist organization.

Trump administration officials met three times with senior Hamas officials, according to sources who spoke to the New York Times, to discuss the release of the last living American Israeli hostage in Gaza, after the president has made clear he wants all hostages to be released.

“The March talks underscored the Trump administration’s ad hoc approach to diplomacy,” the newspaper reported. “But in the face of furious Israeli opposition, Hamas’s hesitation and the Trump administration’s shifting position, an agreement to free the hostage, Edan Alexander, never came together.”

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Six sources familiar with the closed-door meetings told the Times the talks were separate from Israel and Hamas’s attempt to extend their cease-fire, but those deadlocked negotiations left U.S. officials with the impression that Israel would inevitably resume its military operations in Gaza.

“Adam Boehler, a senior U.S. official, wanted Hamas to agree to the release of the last living American Israeli hostage in Gaza so that President Trump could announce his freedom during a speech to Congress,” the Times reported. “The day of the first meeting, after iftar, the fast-breaking meal during the Muslim holy month of Ramadan, three Hamas officials welcomed Mr. Boehler, a private equity investor who was Mr. Trump’s nominee for special envoy for hostage affairs, and his adviser, a recent graduate of Harvard Business School. They met in a sitting room with a large mural of al-Aqsa Mosque in Jerusalem and a picture of Ismail Haniyeh, the Hamas political chief slain by Israel in July.”

Boehler and his adviser shared pastries and freshly squeezed orange juice with Hamas officials Taher al-Nono, Basem Naim and Osama Hamdan, and the Trump envoy returned two days later to speak to the group’s top negotiator Khalil al-Hayya, who said Hamas would ask for the return of only 250 prisoners as a gesture of goodwill, instead of the 500 Palestinians in Israeli custody the group would normally demand.

“During the March meetings, Mr. Boehler was in close contact with Steve Witkoff, Mr. Trump’s Middle East envoy, coordinating positions and providing updates, the two people said,” the newspaper reported. “Before the third and final meeting with Hamas, on March 5, U.S. officials no longer felt their offer was possible. They decided that the most they could propose would be 100 prisoners, without a promise that they would be serving life sentences, for Mr. Alexander.”

Boehler received an angry phone call from Ron Dermer, an adviser to Israeli prime minister Benjamin Netanyahu, who expressed frustration that he had not informed Israel of the talks in advance.

“During the March meetings, Mr. Boehler was in close contact with Steve Witkoff, Mr. Trump’s Middle East envoy, coordinating positions and providing updates, the two people said,” the Times reported. “Before the third and final meeting with Hamas, on March 5, U.S. officials no longer felt their offer was possible. They decided that the most they could propose would be 100 prisoners, without a promise that they would be serving life sentences, for Mr. Alexander.”

Hamas issued a statement indicating that it would release Alexander and bodies of the American Israeli hostages, an offer similar to what Boehler had proposed, but he was no longer negotiating directly with the group, and Israel resumed its bombing campaign days later.