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The Friday release of two American hostages by Hamas illuminated what remains a breakneck endeavor within the U.S. government to negotiate the freedom of others still in captivity, amid grim expectations that an impending Israeli ground invasion of Gaza will render those efforts forbiddingly difficult.

The freeing of Judith and Natalie Raanan was a major breakthrough in the tense, complicated work led by a team from the State Department, FBI and intelligence community. Working with interlocutors in Qatar and alongside counterparts in the Israeli government, U.S. officials passed messages to Hamas in hopes the mother and daughter, who live in the Chicago suburbs, would make it back to safety.

But the race to save the rest is challenged by a host of factors, according to diplomats, officials working on the hostage process and other people familiar with the matter, who spoke on the condition of anonymity to discuss a fragile and anxious process.

The prosecutor of the <a href="https://www.washingtonpost.com/world/2024/04/29/icc-israel-warrants-gaza/" target=_blank>International Criminal Court</a> said he was seeking <a href="https://www.washingtonpost.com/world/2024/05/20/icc-arrest-warrants-netanyahu-sinwar-hamas-leaders/" target=_blank>arrest warrants for senior officials in the Israel-Gaza conflict</a>, including Israeli Prime Minister Benjamin Netanyahu and Hamas leader Yehiya Sinwar, on charges of war crimes and crimes against humanity.

The U.S. government isn’t sure exactly how many U.S. citizens are being held captive. After Friday’s release of the Raanans, 10 Americans remain unaccounted for. Not all of them are presumed to be hostages, one person said. Israel has not yet identified the remains of all the people killed in the initial Hamas assault.

Chief among the challenges ahead: the expectation that once Israel invades, talks will collapse and consideration of the hostages will fall by the wayside.

When asked by reporters on Friday whether Israel should delay its ground invasion of Gaza to allow time for more hostages to be freed, <a href="https://www.washingtonpost.com/elections/candidates/joe-biden-2024/" target="_blank" class="contextual_link">President Biden</a> replied “yes,” an apparent break with the administration’s previous assertions that it would not dictate the timeline on which an attack should commence. The White House later said the president misheard the question and instead was affirming that he wanted more hostages released.

“The urgent work to free every single American, to free all other hostages continues, as does our work to secure the safe passage out of Gaza for the Americans who are trapped there,” Secretary of State Antony Blinken told reporters earlier Friday.

Biden has maintained that securing the hostages’ release is his top priority. About a week after Hamas’s cross-border massacre, Biden spoke with the families of Americans presumed to be held hostage. He did the same on Wednesday, during his seven hours on the ground in Tel Aviv, this time consoling family members of Israeli hostages as well as victims of the attack.

And on Friday, Biden spoke to the Raanans after their release, telling them that “they will have the full support of the U.S. government as they recover from this terrible ordeal,” the White House said in a statement.

While Hamas led the Oct. 7 attack on the Israel-Gaza border, multiple militant groups are now holding hostages, three people who have been briefed on the negotiations said. That has exacerbated the difficulty facing U.S. and other officials directly involved in the process because it’s unclear which groups are holding which hostages, the people said.

Part of the challenge is that, in Hamas’s accounting, after its members tore down the border fence between Gaza and Israel, militants affiliated with several groups rushed through, including members of Islamic Jihad, said a diplomat with insight on the negotiations. Hamas itself claims not to have a full picture of all of the hostages, where they are being held and who is holding them, the diplomat said.

Overall, about 200 people are believed to be in captivity, the Israel Defense Forces said Friday. Many nationalities are represented, including dual nationals who are also Israeli. Israeli officials have a separate negotiation process for their citizens but are working closely with Americans and representative from other governments.

Unrelenting Israeli airstrikes on Gaza also are complicating negotiations and making it more difficult to assess where hostages are being held and whether they are alive, those familiar with the process said. Biden said Friday in his statement hailing the Raanans’ release that efforts to free hostages held by Hamas would continue, a potential sign the White House believes the group does possess additional Americans.

The White House has dispatched Steven Gillen, a longtime Middle East expert in the State Department, to lead the hostage recovery efforts from Israel. He was at Blinken’s side for much of the secretary’s diplomatic engagement over the last week.

Separately, the Biden administration believes that about 500 Americans are trapped inside Gaza, not as hostages but because they were there when the Hamas attack occurred and have been unable to leave amid the Israeli military’s retaliation. U.S. officials are working to secure a safe passage out of Gaza for Americans via the Rafah border crossing into Egypt, but it had not yet opened as of Friday. That initiative depends on the cooperation of the Egyptian government, Hamas and Israel.

The Raanans’ release was a sign that the negotiations were not hopeless, said one person familiar with the U.S. effort.

“It shows that it can happen,” this person said. “At all times, everybody is very cautious around here about being hopeful.”

The person said that in the immediate aftermath of the Hamas assault, U.S. hostage specialists were highly skeptical about their chances of success. The mood changed for the better sometime around last weekend, the person said, declining to be more specific about what caused the shift.

But the situation remains tenuous. Blinken and his top aides have urged the Israelis to allow aid into Gaza, contemplate an end game strategy and work to limit civilian casualties, though they have refrained from asking them to delay their assault, people familiar with the matter said.

Miriam Alster

Biden’s visit to Israel this week may have had that effect, though.

One U.S. official said it was clear that Israeli Prime Minister Benjamin Netanyahu was not going to wait until the hostage crisis was resolved to initiate a ground offensive and that there was little Washington could do to change that calculus. The Israeli leader has continuously bucked U.S. demands during the Biden era and officials are loath to create a public spat as Republicans on Capitol Hill search for any sign of the president being insufficiently pro-Israel.

The U.S. government revamped the procedure through which it navigates international hostage negotiations less than a decade ago, after the families of Americans held hostage in Syria complained of being passed around among government agencies, none of whom seemed capable of communicating information about missing loved ones or coordinating America’s response.

The office of the special presidential envoy was created to effectively answer the key questions underscored by those failings.

“We’re able to come up, maybe ahead of time, with almost our laundry list of things that we might be able to offer in order to break someone through,” Roger Carstens, the special presidential envoy for hostage affairs, told an online audience earlier this year during a talk hosted by the International Spy Museum. Setting up a means to talk to the hostage-takers is critical, Carstens said, but the logistics of different scenarios can create significant obstacles.

“Then you get into the problem of what kind of concessions you can give,” Carstens said. “If it’s a terrorist, there are certain things that we’re not allowed to throw onto the table. For instance, you would not want to put a bag of money on the table to a hostage group.”

There are legal and policy considerations, and congressional stakeholders who must be engaged. In such negotiations, Carstens said, the approach is to “try to sit down and have a real conversation.”

Karen DeYoung contributed to this report.

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Michael Birnbaum is a national security reporter for The Washington Post, covering the State Department and diplomacy. He previously served more than a decade in Europe as The Post’s bureau chief in Brussels, Moscow and Berlin, reporting from more than 40 countries, and he covered climate and security from Washington. He joined The Post in 2008.

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U.S. effort to free Gaza hostages accelerates as ground war looms

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Hamas releases American mother and daughter held hostage after Qatari mediation

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