After a second round of face-to-face negotiations in Istanbul on June 2, it seemed like Russia and Ukraine were further from a cease-fire -- let alone a deal to end the biggest war in Europe since 1945 -- than they had been when they sat down to start the talks.
Days later, the path toward peace may be even longer, and the hurdles higher: Russian President Vladimir Putin lashed out on June 4 after deadly railroad attacks he blamed on Ukraine, branding the government in Kyiv "terrorists" and seeming to question whether talks should continue.
US President Donald Trump, following a phone call with Putin later the same day, said their conversation would not lead to "immediate peace" and that Putin told him Moscow would respond to Ukrainian drone attacks that struck strategic bombers deep inside Russia.
If the first direct peace talks since the weeks after Russia's full-scale invasion of Ukraine in 2022 were not already doomed to failure, are they now? Here's what to watch in the wake of the second round of negotiations, the Ukrainian drone strikes on Russian bombers, Putin's outburst, and his conversation with Trump.
Is Putin's Stance Hardening?
Carried out on the eve of the June 2 talks, the Ukrainian drone strikes were a major display of force. In the ensuing days, a slew of social media posts from Ukrainians and their supporters suggested the attacks showed that Kyiv does hold cards, contrary to a remark Trump made after a disastrous Oval Office meeting with Zelenskyy in February.
But Tatyana Stanovaya, a longtime analyst of the Kremlin and a senior fellow at the Carnegie Russia Eurasia Center, said it would be wrong to expect that the strikes would move push Putin closer to making any concessions. In fact, she said, it may push him in the opposite direction.
"I believe such attacks will only reinforce his determination to dismantle the Ukrainian state in its current form," Stanovaya wrote on X. "He will respond by becoming more hardline and less compliant."
At the same time, Russia would like to keep the direct talks with Ukraine going, observers say, because the negotiations allow Moscow to claim that it is seeking peace, a move that helps keep Washington from imposing a new round of sanctions.
Anyone who watched Putin speak at a government meeting on June 4 might think Moscow was about to abandon the process after two meetings in Istanbul on May 16 and June 2.
"Who even holds negotiations with those who rely on terror, with terrorists?" said Putin, who described Ukraine's leadership as "the heads of a thoroughly rotten and completely corrupt regime."
Bellicose words, but not necessarily words that suggest a change in diplomatic strategy. Russia has maintained an uncompromising stance for months, laying out maximalist terms at the Istanbul talks and rejecting calls by Kyiv and the West for a 30-day cease-fire.
Moscow has made clear it opposes Ukrainian President Volodymyr Zelenskyy's push for a summit with Putin, and top Kremlin foreign policy aide Yury Ushakov indicated the remark about terrorists meant that Russia would indeed reject any further direct talks.
Putin told Trump that the June 2 negotiations were "useful" and "we hope that…the two sides will be able to continue their talks" after they study the proposals Russian and Ukrainian negotiators exchanged at the meeting.
Following the meeting, the head of Ukraine's negotiating team, Defense Minister Rustem Umerov, proposed further talks between June 20 and June 30. Zelenskyy sharply criticized Russia and after a drone attack on the Chernihiv region killed a woman, her adult daughter, and her year-old grandson, but he did not say whether it would affect any further talks with Moscow.
"So far, it seems like the Ukrainian attacks on Russian territory won't have any consequences for the talks in Istanbul," Russian-language news outlet The Bell wrote in a newsletter late on June 4.
"There's not much to undermine, because serious results from the current talks should not be expected," it said, before adding that results "are needed by both sides to demonstrate their peaceful intentions to Donald Trump."
Will Trump Pressure Putin?
A crucial question, as it has been for months, is how Trump will react to the latest developments and whether he will step up US pressure on Russia, something he has refrained from doing so far.
Trump, who has been seeking to broker an end to Russia's war on Ukraine since he took office for a second time in January, has said several times that he believes Putin wants peace.
But he has voiced increasing frustration with Putin in recent weeks as Russia has pounded Ukraine with relentless attacks, often killing civilians, and rejected the 30-day cease-fire proposal, which initially came from Washington and was accepted by Kyiv.
Putin "has gone absolutely CRAZY! He is needlessly killing a lot of people, and I'm not just talking about soldiers. Missiles and drones are being shot into Cities in Ukraine, for no reason whatsoever," Trump wrote on his Truth Social platform on May 26.
Two days later, Trump warned that the United States will take unspecified actions if he determines that Putin is "tapping us along" rather than engaging in a good-faith search for peace, adding that "it will take about a week and a half, two weeks."
While Trump has also continued to criticize Ukraine at times, his remarks about Putin have raised expectations that he could impose new sanctions on Russia. On June 4, he posted a recent Washington Post opinion article headlined "Congress can give Trump the leverage to coerce Putin" -- a reference to a bipartisan bill that Republican Senator Lindsey Graham has said would impose "bone-crushing" sanctions on Russia.
But after his phone call with Putin the same day, which he said was a "good conversation, but not a conversation that will lead to immediate peace," Trump made no mention of any frustration with Russia or its president.
In a Truth Social post devoted less to the war in Ukraine than to the possibility that Putin could help reach a deal curbing Iran's nuclear program, Trump said that he and Putin had discussed "attacks by both sides," Moscow and Kyiv.
And he conveyed what he indicated was a strongly worded warning from Putin that Russia "will have to respond to the recent attack on the airfields" -- something Putin had not mentioned in public at all.
The threat of tougher sanctions still hangs in the air, and Trump's next steps are unclear, but the absence of any words of warning for Putin or Russia in his post rattled Ukrainians and angered his opponents at home.
"Trump, by effectively refusing to respond firmly to Putin's threats against Ukraine, has replaced the previous 'Putin, stop' stance with a silent 'Go ahead, Putin: Do it, and we won't stop you,'" Kyiv-based political scientist Oleh Saakyan told Current Time.
Later on June 5, meeting with German Chancellor Friedrich Merz in Washington, Trump said that he had urged Putin not to hit at Ukraine over the drone strikes but that he expects Russia will do so. "It's probably not going to be pretty. I don't like it," Trump said.
Zelenskyy, meanwhile, redoubled his calls for increased pressure on Russia following the deadly strike in the Chernihiv region, saying, "We expect action from the United States, Europe, and everyone in the world who can really help change these terrible circumstances.
"Strength matters, and the war can only end through strength," he wrote on X. "Moscow must be pressured by all available means and gradually deprived of its ability to continue this aggression."
Meeting with Trump at the White House, Merz echoed Zelenskyy, calling for more pressure on Moscow and saying the US president is the "key person in the world" in that regard.
Trump made no commitment to ramp up the pressure and declined to say whether he supports the Senate sanctions bill, calling it "very harsh." He said he told Putin that Russia's war on Ukraine was like two children "fighting in a park. Sometimes you're better off letting them fight for a while and then pulling them apart."
Trump suggested that he believes it is still too early to impose new sanctions over the war -- and that if the time comes, he might target both sides.
"When I see the moment where it's not going to stop... we'll be very, very, very tough. And it could be on both countries, to be honest," he said. "You know, it takes two to tango."
