By issuing strict and rigid demands during discussions for peace with Ukraine while simultaneously bombarding it with missile and drone attacks, Russian President Vladimir Putin communicates a straightforward message: he is determined to secure a resolution that aligns with his terms and will persist in conflict until those terms are met.

At the same time, he endeavors to avoid frustrating U.S. President Donald Trump by lauding his diplomatic efforts and indicating Moscow’s willingness for peace discussions — even as he asserts extreme conditions that are dismissed by Kyiv and Western powers.

Trump, who previously vowed to resolve the ongoing war within 24 hours, has disrupted the U.S. stance of sidelining Russia by engaging in conversations with Putin and criticizing Ukrainian President Volodymyr Zelenskyy. Nevertheless, Trump has simultaneously cautioned Putin against “playing games” and has issued threats of sanctions against Moscow if it does not support his peace initiatives.

Trump says Putin is ‘playing with fire’

In recent days, Trump signaled he was losing patience with Putin, declaring the Russian leader had gone “crazy” by stepping up aerial attacks on Ukraine. He also said: “What Vladimir Putin doesn’t realize is that if it weren’t for me, lots of really bad things would have already happened to Russia, and I mean REALLY BAD. He’s playing with fire!”

Dmitry Medvedev, a former Russian president who serves as deputy head of Putin’s Security Council, fired back: “I only know of one REALLY BAD thing — WWIII. I hope Trump understands this!”

Fyodor Lukyanov, a Moscow-based analyst familiar with Kremlin thinking, said Putin is engaged in a “psychological game” with Trump, with both men thinking they understand each other well.

“Putin’s tactics is apparently based on an assumption that the issue has a lesser priority for his interlocutor, who wants to get rid of it one way or another, while for the Russian side, nothing compares to it in importance,” Lukyanov wrote a commentary. “In this logic, the one who sees it as something of lesser importance will eventually make concessions.”

While Ukraine’s European allies urge Trump to ramp up sanctions against Moscow to force it to accept a ceasefire, some fear that Trump may end up distancing the U.S. from the conflict. If the U.S. halts or reduces military aid to Kyiv, it would badly erode Ukraine’s fighting capability.

Growing Russian pressure

Kyiv already is experiencing a weapons shortage, particularly air defense systems, leaving it increasingly vulnerable to Russian missile and drone attacks.

Across the over 1,000-kilometer (over 600-mile) front line, the exhausted and outgunned Ukrainian troops are facing increasing Russian pressure. This month, Russian forces accelerated their slow push across the Donetsk region, the focus of Moscow’s offensive, grinding through Ukrainian defenses at the quickest pace since last fall. Russia also expanded its attacks in the northeastern Sumy and Kharkiv regions following Putin’s promise to create a buffer zone along the border.

Many observers expect Russia to expand its offensive over the summer to try to capture more land and set even tougher conditions for peace.

“Moscow thinks its leverage over Ukraine will build over time, and since Trump has strongly implied that he will withdraw from negotiations the Russian military is set to intensify its operations,” said Jack Watling of the Royal United Services Institute in London. He predicted Russia would intensify efforts to take all of the Donetsk region while also pressing a bombing campaign.

“The Kremlin will want to suggest a deteriorating situation as negotiations continue and to signal to Europe that the rear is not safe, to discourage European militaries from putting forces in country,” Watling said in an analysis.

Sergei Markov, a pro-Kremlin, Moscow-based analyst, said the long-expected offensive hasn’t yet begun in earnest as Russia is cautious not to anger Trump. “If Kyiv derails peace talks, the Russian army will start a big offensive,” he said.

Putin’s conditions for peace

Putin has demanded that Ukraine withdraw its forces from Donetsk, Luhansk, Zaporizhzhia and Kherson — the four regions that Russia illegally annexed in September 2022 but never fully controlled. That demand had been rejected by Kyiv and its allies, but the Russian delegation reportedly repeated it during talks with Ukraine in Istanbul on May 16.

Those talks, the first since botched negotiations in the opening weeks of the war, came after Putin effectively rejected a 30-day truce proposed by Trump that was accepted by Kyiv. Russia had linked such a ceasefire to a halt in Ukraine’s mobilization effort and a freeze on Western arms supplies.

Putin proposed talks to discuss conditions for a possible truce. Trump quickly prodded Kyiv to accept the offer, but the negotiations yielded no immediate progress except an agreement to exchange 1,000 prisoners each.

Russia offered to hold another round of talks Monday in Istanbul, where it said it will present a memorandum setting conditions for ending hostilities. It refused to share the document before the negotiations.

Some observers see the talks as an attempt by Putin to assuage Trump’s growing impatience.

“Putin has devised a way to offer Trump an interim, tangible outcome from Washington’s peace efforts without making any real concessions,” said Tatiana Stanovaya of the Carnegie Russia Eurasia Center.

Facing Western accusations of stalling, the Kremlin responded that the conflict can’t be resolved quickly and emphasized the need to address its “root causes.”

When Putin invaded Ukraine, he said the move was needed to prevent Ukraine from joining NATO and protect Russian speakers in the country -– arguments strongly rejected by Kyiv and its Western allies as a cover for an unprovoked act of aggression.

Along with those demands, Putin also wants limits on Ukraine’s sovereignty, including the size of Ukraine’s military, and for Kyiv to end what Moscow sees as glorification of Ukraine’s World War II-era nationalist leaders, some of whom sided with the invading forces of Nazi Germany over the Soviet leadership in the Kremlin.

A Kremlin negotiator who’s been there before

Seeking to underline that Moscow will press home its initial demands, Putin appointed his aide Vladimir Medinsky to lead the Russian delegation in Istanbul. He also led the Russian side in the 2022 talks. Kyiv reportedly has asked the U.S. to encourage Putin to replace him.

The soft-spoken, 54-year-old career bureaucrat, who was born in Ukraine, ascended through the Kremlin ranks after writing a series of books exposing purported Western plots against Russia.

In an interview with Russian state television after the May 16 talks, Medinsky pointed to Russia’s 18th century war with Sweden that lasted 21 years, a signal that Moscow is prepared to fight for a long time until its demands are met.

“History repeats itself in a remarkable way,” he said.