The two sides have met once so far, in Islamabad, while the second round of talks was postponed. On Monday, Trump declared on social media that the deal his administration will finalize will be “FAR BETTER” than the previous deal, which he called “one of the Worst Deals ever made having to do with the Security of our Country.”

White House press secretary Karoline Leavitt confirmed Friday that Trump’s son-in-law, Jared Kushner, and special envoy Steve Witkoff are headed back to Pakistan for a second round of talks. Vice President JD Vance is not traveling there, even though he did for the first round of talks, because Iranian Parliament Speaker Mohammad-Bagher Ghalibaf will not be in attendance.

What was the 2015 agreement?

The 2015 Iran nuclear deal was not just between the U.S. and Iran. It included the five permanent members of the United Nations Security Council — China, France, Russia, the United Kingdom, and the U.S. — and Germany, collectively known as the P5+1, as well as the European Union.

When the deal went into effect in January 2016, it required Iran to give up most of its nuclear material, dismantle two-thirds of its centrifuges, which are the device used to enrich uranium to a potent form for use in a nuclear weapon, a cap to the number of centrifuges it would operate at a time, and the deal barred Iran from enriching uranium until 2030 beyond a level of 3.67%.

Iran also disabled a nuclear reactor and agreed to allow the International Atomic Energy Agency to inspect its facilities to ensure compliance. The U.S. and Europe lifted many of the sanctions that had been in place against Iran, and tens of billions of Iran’s foreign assets were unfrozen.

Critics of the deal argued that putting timelines on many of the clauses had an expiration date of 2030, which would effectively allow them to increase their nuclear program after, though Obama officials said at the time there would be time before the expiration to negotiate an extension.

Trump pulled out of the deal in 2018, three years after it went into effect, and reimposed sanctions. In response to Trump’s withdrawal, Iran rapidly increased its nuclear activity.

He returned to the White House in a much different world. Iran’s proxies had gone to war with Israel during the Biden administration, though Iran had largely avoided the conflict. The U.S. and Israel went to war against Iran in the 12-day war last June, and Trump’s administration sought renewed negotiations ahead of the start of this war on Feb. 28.

The Trump administration, in justifying the war now, said Iran posed an “imminent” threat.

CIA Director John Ratcliffe told lawmakers this spring that Iran possesses more than 950 pounds of “highly enriched uranium at 60% weapons grade that would be capable of putting together 10 nuclear weapons,” believed to be buried under the rubble at the nuclear facilities U.S. forces targeted in Operation Midnight Hammer last year.

Trump has long derided the Iran nuclear deal for the money given to Tehran. While the president and the deal’s critics bring up the U.S. shipment of $1.7 billion in cash to Iran, it pales in comparison to the $50 billion in Iranian funds abroad that were unfrozen.

The origin of the money dates back to a $400 million U.S. arms sale to Iran prior to the 1979 Islamic Revolution, and the U.S. government subsequently refused to deliver the arms while Iran had long demanded reimbursement. That money accrued $1.3 billion in interest as it was disputed over the last several decades. They had to use cash because U.S. sanctions limited Iran’s access to the global financial systems.

How is Trump’s plan different?

Unlike the 2015 JCPOA, Trump wants to address several matters, not just Iran’s nuclear program, and the broader array of subjects will likely pose even more hurdles.

The Trump administration wants to limit Iran’s missile capacity, obtain the deeply buried, highly enriched uranium, and get it to agree to stop its funding of proxy forces across the region that include the likes of Hamas in Gaza, Hezbollah in Lebanon, the Houthis in Yemen, and militias in Iraq.

Getting Iran to agree to those points will be a significant task, especially considering Tehran has never previously agreed to such constraints.

“The Iranians will not compromise on proxies, which is part of Trump’s demand,” Aaron David Miller, a longtime State Department Middle East official, told the Washington Examiner. “They will not compromise on ballistic missiles, which is part of Trump’s demand. And now they have demonstrated for all the world to see that they can close the straits whenever they want.”

The president has said he wants the Iranians to completely stop enriching uranium, which is a more aggressive stance than the original deal, which allowed for them to do it. Iranian Foreign Minister Abbas Araghchi, who was one of the lead negotiators for the first round of talks, called Iran’s right to enrich uranium nonnegotiable before the war.

While it has not been referenced publicly yet, the administration could attempt to pursue two separate deals with Iran to make it easier to navigate.

“My guess is the Trump administration is prepared to pursue the nuclear issue separately, just as the Obama administration would pursue nuclear apart from the other issues,” Robert Einhorn, a longtime State Department official who worked on Iran nuclear policy prior to the 2015 agreement, told the Washington Examiner. “I think the Obama administration was right to focus the negotiations on the nuclear issue that was the most urgent threat, and it would have taken much longer, and it would be much more complicated to include missiles and proxies in the JCPOA negotiations.”

Einhorn, who served as the State Department special adviser for nonproliferation and arms control until 2013, said the Obama administration “didn’t give sufficient priority to dealing with those other threats,” though he also acknowledged he is “not sure” what the Trump administration could actually achieve on the non-nuclear issues.

Despite the president’s criticism of the money given to Iran in the original deal, the Trump administration is considering the possibility of unfreezing $20 billion of Iranian money in the negotiations, according to the Washington Post.

Possible hiccups

Trump acknowledged Thursday that the U.S. does not “know who the leader is in Iran,” which presents a difficult challenge in determining who ultimately has the authority to agree to a deal.

In the early stages of the war, Ayatollah Ali Khamenei and several other high-ranking officials in the military and political ranks were killed. Iran’s Assembly of Experts selected Mojtaba Khamenei to succeed his father as supreme leader, but he has not been seen publicly since he was appointed more than a month ago, though he was reportedly injured and disfigured in the strikes that killed his father.

The Islamic Revolutionary Guard Corps has remained a powerful force in the country, even though it, too, has been weakened.

Mojtaba Khamenei’s absence from public life has raised speculation that he could be incapacitated or dead. Maj. Gen. Ahmad Vahidi has taken over as commander of the Guard after the killing of his predecessor, and he is viewed as a hard-liner who does not want to negotiate with the U.S.

War Secretary Pete Hegseth said this month that the U.S. had seen Iran attempt to dig through the rubble left by U.S. strikes at missile production and storage facilities.

“As long as this regime remains in power, you are never going to be able to say they are not still thinking about or even working toward restoring where they were,” said Miller, now a senior fellow at the Carnegie Endowment for International Peace.

HARD-LINE IRANIAN REVOLUTIONARY GUARD COMMANDER EMERGES AS KEY PLAYER

If Vahidi, another Guard official, or Khamenei is the ultimate decision-maker in Iran, it will be hard to get a deal done, given neither side’s apparent willingness to compromise. However, there may be officials who are more moderate and willing to negotiate.

“You have a supreme leader,” said Einhorn, who now works for the Brookings Institution. “We don’t know how influential he is at this stage, but you know his father, his wife, his child were all killed. He’s been apparently disfigured by it. He’s thinking of revenge, I would assume, and he’s surrounded by an increasingly influential IRGC that has no interest in compromises. So at this stage, I think it would be a foolish bet to assume that there’s going to be a very important and beneficial deal negotiated in the next few months.”