In his first term, President Donald Trump met with Russia’s Vladimir Putin six times but one moment stood out.

It happened in Helsinki, Finland, in 2018 when Trump, standing next to him, suggested he believed Putin’s denial that Russia interfered in the 2016 election over the findings of U.S. intelligence.

At the time, Trump said U.S.-Russia relations had “never been worse” than before they met but that had “changed.”

Now, Trump is set to hold his first one-on-one meeting with Putin of his second term at Joint Base Elmendorf-Richardson in Anchorage, Alaska.

The backdrop for Friday’s highly-anticipated summit is a darker one, amid Russia’s relentless onslaught on Ukraine and Putin presenting a frustrating obstacle to Trump’s professed desire to end the war.

The meeting will spotlight their relationship — one that Trump said during the 2024 campaign was so strong he could end the conflict on his first day in office or even before.

“It seems that Donald Trump used to think that he understands Putin well and has a good rapport with him, but over the last few months we’ve seen him alter his position in that regard and actually become more frustrated with Putin. I think he’s becoming more moderated in his expectations about what the meeting can bring,” said Maria Snegovaya, a senior fellow for Russia and Eurasia with the Center for Strategic and International Studies.

Trump called Putin a “strong leader” in his first term and a “genius” shortly after his forces first invaded Ukraine.

Early in his second term, Trump said that Putin would be “generous” in peace talks and Ukraine more difficult.

Trump made several public demands of Ukraine, including that it would have to give up its goal of joining NATO and possibly cede some territory, while notably not setting any such red lines for Russia.

The president even sympathized with Putin’s status as a global pariah, saying in February that he would “love” for Russia to rejoin the Group of Seven nations and that it was a mistake for Moscow to have been expelled from the company of world leaders following Putin’s annexation of Crimea.

“Look, nothing’s going to happen until Putin and I get together, OK?” Trump said back in the spring.

Over the last few months, however, Trump’s tone toward Putin has shifted.

“I’ve always had a very good relationship with Vladimir Putin of Russia, but something has happened to him. He has gone absolutely CRAZY!” Trump wrote on his social media platform in late May.

Trump expressed repeatedly that he’s “disappointed” in the Russian president as strikes intensified between Russia and Ukraine this summer.

In July, Trump said he was fed up with the “bull—- thrown at us by Putin.” “He’s very nice all the time, but it turns out to be meaningless,” he said.

“We’re not happy with Putin. I’m not happy with Putin. I can tell you that much right now, because he’s killing a lot of people,” Trump added.

Trump has kept American-made weapons supplied to Ukraine through a deal with European partners and recently slapped steep secondary tariffs on India, one of the largest purchasers of Russian oil, in indirect pressure on Moscow.

Still, Trump held back on his threats to impose harsher sanctions on Aug. 8 if Putin did not agree to a ceasefire. Instead, on that date, Trump announced he would host the Russian leader on U.S. soil for a one-on-one meeting.

“He has more that he could do in order to push Putin to come to the table,” said William Taylor, a former U.S. ambassador to Ukraine currently serving as a senior fellow at the Atlantic Council.

So far, Trump has tempered expectations about Friday’s summit. He’s called it a “feel-out meeting” and the White House described it as a “listening exercise.”

At the same time, he warned again this week of “severe consequences” if Russia didn’t end the conflict.

“I think that Trump believes that strongmen of Putin’s kind are to be negotiated with eye to eye, and he wants to feel the ground to see what he gets from the meeting with Putin. The problem with that is Putin is also a shrewd manipulator and he has the KGB background, he is known to be very convincing and make people like him in person,” said Snegovaya.

John Bolton, Trump’s former national security adviser, said Putin’s goal for this summit is to get back into Trump’s good graces.

“What Putin wants to get back, he’s not so worried about the sanctions, he wants the relationship back with Trump. We’ll see if he gets it,” Bolton said on ABC’s “This Week.”