As Steve Witkoff, U.S. President Donald Trump’s “envoy for everything,” sits down again with a top Iranian diplomat this weekend, he confronts one galactic diplomatic lift. In Rome, Witkoff will face off against Iranian Foreign Minister Abbas Araghchi, a skilled nuclear negotiator from a repressive authoritarian regime that has been badly weakened by Israel and is in no mood for dramatic concessions, let alone capitulation to Washington.

At home, Witkoff is surrounded by the president’s hard-line advisors—who don’t believe an agreement is possible—and an impatient, impulsive president who wants a quick deal and is threatening the use of force if he can’t get one. The first meeting, in which everyone seemed to abide by Emily Post’s guide to good table manners, will be unlikely to be repeated this coming weekend as the diplomatic bromides give way to much tougher positions.

Here are five politically inconvenient realities likely to govern the negotiations.

A Problem With No Solution

First, let’s be clear: There are no great deals, good options, or Hollywood endings when negotiating with Iran on the nuclear issue.

Witkoff is dealing with a brutal regime that imprisons and tortures its own citizens; espouses its revolutionary ideology in at least four Arab capitals; supports terrorism around the region; funnels drones for Russia’s strikes against Ukraine; and feeds on a diet of antisemitic, anti-American, and anti-Israeli rhetoric to legitimize its rule and mobilize its hard-line supporters. Trump is likely to discover sooner rather than later that Iran is a strategic problem for the United States with no strategic solution.

The only way to guarantee that Iran would never acquire a nuclear weapon would be a change in regime so fundamental that it would have no need or desire to weaponize. Despite Iran’s weakened state, it’s hard to imagine such a development anytime soon; indeed, there’s no guarantee that the end of clerical rule wouldn’t give way to a more militant and militarized elite even more desirous of a nuclear weapon.

Forget doing transformational diplomacy with this regime, which could cover the nuclear program, support for proxies, and ballistic missiles all wrapped up in one neat package. It took two years to produce the functional but flawed 2015 Joint Comprehensive Plan of Action (JCPOA), which focused only on the nuclear issue.

Instead, this time, think transactional diplomacy and interim accords, and yes—in a word that Trump loves—think deals. At least for now, it’s clear that both Trump and his envoy are focused on the narrow issue of preventing Iran from acquiring a nuclear weapon.

“I’m not asking for much,” Trump asserted earlier this month, “but they can’t have a nuclear weapon.” Indeed, in the first of several ironies, despite some mixed messaging recently, Witkoff sounds like a guy who may actually have read the JCPOA (the agreement Trump despised) and wants to hold Iran to its terms, at least when it comes to how much uranium Iran is permitted to enrich.

Iran Is Vulnerable but Also Defiant

Second, to paraphrase Charles Dickens, it may well be both the best and worst of times for U.S.-Iran diplomacy.

On the upside for Washington, the Iranian economy is in shambles as a result of sanctions, corruption, and mismanagement. And Iran’s aging and ailing supreme leader is facing the uncertainties of succession as well as a young population eager for economic prosperity and engagement with the rest of the world. At the same time, Iran’s position in the region has worsened dramatically as two of its proxies—Hamas and Hezbollah—have been hollowed out by Israeli military power, and Tehran’s own ballistic missile production and air defenses have been demolished by Israeli strikes.

Enter a new, unpredictable U.S. president who was threatening military action unless Iran agreed to begin negotiating. It was the latter factor that reportedly overcame Supreme Leader Ali Khamenei’s staunch opposition to negotiating with the Trump administration; indeed, the message by his advisors was that unless Iran began talks, the Islamic Republic’s rule could be toppled, according to two senior Iranian officials familiar with the deliberations.

None of this meant that Iran was ready to make deep concessions, let alone capitulate. The supreme leader’s anger, hatred, and distrust of the United States, especially the Trump administration, runs deep. After all, it was the first Trump administration that killed Qassem Suleimani (a wrenching loss for the supreme leader) and who pulled out of the JCPOA, instead imposing maximum pressure sanctions on the regime.

Iran’s nuclear program has made major advances in the past seven years, which the regime would be reluctant to give up, particularly at a time when it appears so vulnerable. Indeed, for the first time, there’s been open debate within Iran on the merits of actually producing a weapon as well as pressure from elements within the Islamic Revolutionary Guard Corps to weaponize. Many now publicly take pride in the country’s capacity to build a bomb.

How the pros and cons balance out with regard to a propitious environment for success of talks is hard to predict. Our colleague at the Carnegie Endowment for International Peace, the veteran Iran analyst Karim Sadjadpour, made the compelling case that “since 1979, Iran has only compromised when it feels the regime’s existence is potentially at stake and it is presented a credible diplomatic exit.”

And the combination of stick and carrot, coercion and diplomacy, needs to be built over time, in Sadjadpour’s view—over months, not weeks. The challenge is an obvious one. Trump, a transactional man, is in a hurry.

Better Than the Last One?

Third, Trump needs an outcome that he can justifiably claim is better than the deal that he walked out of. That won’t be easy.

The fact the administration seems a bit confused and divided on exactly what it wants out of Iran negotiations should hardly come as a surprise. This is a president whose policies seem guided by impulse over strategy. Already, there appears to be a split between some of his hard-line advisors, who want to dismantle Iran’s nuclear program, and the president’s special envoy, who—along with Trump—seems more focused on a rigorous verification program to keep the Iranians away from a nuclear weapon.

Nor is the detailed agenda for these negotiations yet to be determined.

This weekend’s meeting should speak volumes about how far apart Iran and the United States are when it comes to determining the terms of the negotiations—essentially, talks about talks. Will proxies, ballistic missiles, massive sanctions relief, or human rights be on the table?

Assuming that an agreement can be reached on what the negotiations and a putative agreement are meant to achieve, the central challenge will become clearer. Is there a way to conclude an agreement—a “Trump accord”—that doesn’t call for complete dismantling of Iran’s nuclear program but can credibly improve the terms of the JCPOA when it comes to keeping Iran away from a bomb? And what is the U.S. expected to provide to Iran in return?

That objective has been made all the more difficult by Trump’s railing against the JCPOA as an accord that was, in his words, “defective at its core.” But it is more than likely that any new Trump accord would strengthen, rather than discard, some of the verification, monitoring, and restrictions contained in the original deal.

The Israel Factor

Fourth, Israel may have delivered Iran and its proxies a decisive and humiliating blow. But Israeli Prime Minister Benjamin Netanyahu’s hand with the United States is decidedly weaker.

This might seem counterintuitive. After all, in his first three months after returning to office, Trump has allowed Netanyahu to have his way in Gaza, delivered all sorts of military assistance that had been delayed by the Biden administration, dropped sanctions on Israeli settlers, and turned a blind eye to an expansion of West Bank settlements and settler violence against Palestinians.

But Iran is a much bigger play for Trump.

The fact that Trump chose to announce the beginning of direct US-Iran negotiations while sitting next to the Israeli leader was a sign of how times may be changing. For the second time (the first was the administration’s dialogue with Hamas earlier this year), Washington opened a direct channel to Israel’s main adversaries. Trump is not about to throw Israel under the Iranian bus, but the administration’s actions suggest that the president is prepared to explore different avenues to get a deal. It also reflects the reality that Trump won’t be quick to buy Netanyahu’s talking points that only military action will stop Iran from getting a bomb.

It’s ironic that it was Israeli military strikes on Iran and the fear of U.S. ones that likely brought Iran to the negotiating table and created a potential nightmare for Netanyahu. The Israeli leader may yet succeed if diplomacy fails. Indeed, Trump has more than once suggested that Israel might take the lead in any military strike.

But for now, Netanyahu doesn’t have many cards to play. Trump more than likely won’t buy Netanyahu’s view that Iran’s entire nuclear infrastructure must be dismantled. Should an agreement be reached that doesn’t meet Israel’s requirements, Netanyahu would be hard pressed to block it. This isn’t 2015, when Netanyahu could make an end run around the Obama administration on Iran and take his case directly to the more friendly, anti-Iran Republican Party. Trump is the GOP, and there’s no higher court of appeals for Netanyahu.

Different Clocks

Finally, perhaps the biggest challenge as we watch U.S.-Iran negotiations play out is the different conceptions of time.

Impatient and impulsive by nature, Trump wants the deal done yesterday, or at least within two months. He’s already expressed concern that Iran may be “tapping” him along and dragging things out. For the Iranians, negotiations likely have two speeds—slow and slower. They don’t trust Trump and want to probe and test, and perhaps figure out a way to bring Russia in on their side. (Araghchi visited Moscow after his first round of talks with Witkoff, and he is going back before round two begins.)

Some argue that the Iranian game is to string out the talks beyond October, when the so-called “snapback provisions” of the JCPOA, which would reimpose all previous sanctions in the event of “significant non-performance by Iran of JCPOA commitments,” would expire. If this is the approach, then Iran might offer up a few interim caps on its enrichment in return for Trump’s dialing back some of his maximum pressure campaign so that Tehran could defuse the immediate threat of military action and buy time to test whether a broader accord is possible.

On the other hand, should the snapback be triggered and all sanctions restored, Iran would likely shut down negotiations and withdraw from the Treaty on the Nonproliferation of Nuclear Weapons, which would almost certainly set the stage for possible military strikes—either by Israel, the United States, or both.

Matters don’t look especially encouraging. Indeed, Iran is closer to a bomb and yet weaker than ever before. Israel is supremely confident that it could manage a successful strike, even though the U.S. intelligence community assesses that one would only set back the program by a matter of months. The U.S. president has deployed a massive show of force in the region and is talking openly of a military strike should negotiations fail.

On the eve of the second round of talks, it’s impossible to say if an agreement is possible. But this much seems clear. Since 2018, when Trump walked out of the JCPOA, the two sides have operated in an environment in which there was no agreement. Despite four Iranian and Israeli strikes on one another’s territory, there was no attack on Iran’s nuclear sites and no massive escalation.

We’d both hazard a guess that if they can find a way through at the negotiating table, both Trump and Iran would like to keep it that way.