President Donald Trump has often bragged about his warm relationship with Russia’s Vladimir Putin. But in the months leading up to the leaders’ first meeting in six years, Trump began asking Europeans and White House aides what’s changed about his counterpart.

The line of questioning, described to CNN by three people familiar with the matter, speaks to Trump’s growing frustration with Putin leading up to their summit in Alaska Friday to discuss ending Russia’s years-long invasion of Ukraine. Trump promised to quickly broker a peace deal even before he took office. Not only has Putin resisted ceasefire proposals, but Russia has escalated its attacks on Ukraine this year.

While there have been some indications that Putin’s short-term objectives in Ukraine may have shifted – underpinning an optimism within the White House that an agreement can be reached – the prevailing view of the US intelligence community is far more skeptical.

Putin maintains the same maximalist territorial goals as he has throughout the war and would likely use a ceasefire to refit his forces and possibly even make another run at Kyiv, multiple people familiar with recent US intelligence reporting on Russia said. And despite European calls for security guarantees for Ukraine, Putin still wants to ensure that Ukraine never joins NATO and that foreign peacekeepers don’t enter the territory, the people said.

“Putin thinks he is winning, so he has no reason to bend,” said one person familiar with the recent US intelligence assessments, who, like others in this story, spoke on the condition of anonymity to discuss sensitive matters. “His thinking is he might as well pocket the wins he has now, including the Ukrainian territory he has already taken by force, and then make another run to take more later,” the person said.

Trump’s desire to better understand Putin comes amid Ukrainian and European concern that the White House is being manipulated by the Kremlin, handing Putin a victory on the global stage by agreeing to meet with him on American soil and without Ukrainian President Volodymyr Zelensky present.

“Russia is offering to stop the war if they get everything they have always wanted, including their most maximalist demands,” a European official told CNN. “And that would not be a deal, it would be a submission.”

Still, some Europeans also believe that Trump may have a unique ability to strike a deal, and they are encouraged by his shifting policy on the war in recent months.

Trump on Wednesday warned that Russia would face “very severe consequences” if he determines that Putin is still not serious about ending the war with Ukraine. Trump didn’t specify what those consequences might be, but he has previously threatened Moscow with stiffer economic sanctions or tariffs.

CNN reached out to the White House for comment.

Putin intelligence remains a ‘hard target’

Discerning Putin’s intentions has been historically difficult. A former officer in the KGB, the Soviet Union’s main security service, Putin keeps an extremely tight circle of confidants and it’s unclear who he is listening to at any given time, according to a person familiar with recent US intelligence reports.

Decades spent trying to decode Putin have given the US tremendous institutional knowledge of the man. Still, US spy agencies have a notoriously poor view of his day-to-day decision-making, multiple officials told CNN. The Kremlin remains what intelligence officials call a “hard target” – incredibly difficult to penetrate through traditional espionage.

But the US has at times successfully gained insight into Putin’s plans, such as his decision to invade Ukraine in 2022. Other foreign intelligence services at the time cast doubt on American warnings that the Russian leader was about to start a war.

Trump has in the past expressed skepticism of the US intelligence community, particularly its assessments related to Russia, and it’s unclear how much he’ll rely on intelligence reports going into Friday’s summit. One US official familiar with recent intelligence analysis questioned whether Trump’s briefers were laying out the hard truths of the situation, including the widely-held view that Putin believes it’s in his best interest to continue the war.

Trump remains confident he can personally and rapidly assess Putin, saying on Tuesday that he’ll know after “probably the first two minutes” of their sit-down if an agreement can be reached to end the war.

“I got along very well with President Putin,” Trump said of his first term, adding that Friday’s summit would be a “feel-out” meeting.

But while Trump has questioned if Putin has changed, others have noticed an evolution in Trump when it comes to his thinking about the Russian.

“European allies say the one who changed is Trump, both in his comfort level in his job and in his understanding of who Putin is,” said one US official, adding that Trump has continued altering his thinking on Russia since he took office earlier this year.

“His approach in early January was naïve … Now Europeans say he finally gets it that Putin is a murderous leader,” the US official said.

Trump’s rising anger with Putin began earlier this summer, coming as Special Envoy Steve Witkoff, Trump’s primary interlocutor with Russia, was also expressing frustration with the Kremlin, said a person familiar with the matter. Witkoff privately commented that the Russians were “tapping us along,” the person said.

Trump also began using frequent expletives when talking about Putin in private meetings, said people in those meetings. It was clear that Trump’s perspective was changing, they said.

“His anger was palpable,” said one person privy to a private meeting between Trump and a European leader.

There are some signals that Putin’s short-term goals may have shifted with an openness to pocketing territorial gains in Ukraine and also shoring up economic deals for Russia, said a source familiar with the intelligence. But it is unlikely that Putin would take that position early-on in any negotiation.

In the final weeks of the Biden administration, US intelligence officials cautioned now-senior advisers to Trump that controlling Ukraine remained Putin’s top priority next to his own regime’s survival, according to a person familiar with the conversations. The officials also warned that the Russian president was eager to exploit any perceived rush to negotiations, the person added.

Putin had bet all his chips on Ukraine and showed no sign of relenting, no matter the costs, the intelligence officials told Trump’s advisors, according to the person familiar with the discussions.

Though analysts have said that Putin’s imperial ambitions regarding Ukraine were long-established, Trump’s aides have told the president that the coronavirus pandemic is at least partly responsible for any change in Putin since he last met Trump in 2019, according to three people familiar with the matter.

The discussion about Putin’s possible shift came as Trump was perplexed about why he had been unable to get Putin to agree to end the Ukraine war.

“Many around Trump are now trying to give him the idea that Putin changed so he has a reason to say that he wasn’t wrong in his initial impression coming into office that Putin is a good guy,” said a person familiar with the matter.

Putin’s pandemic isolation

Leading up to the Russian invasion of Ukraine in 2022, some US intelligence officials believed that Putin was becoming more paranoid – perhaps due to protracted isolation during the pandemic.

He rarely left his palatial residence outside Moscow during the pandemic. His public appearances were largely limited to televised video conference meetings with Russian cabinet officials. Anyone Putin met with in person had to first quarantine for two weeks, including World War II veterans who shared an outdoor stage with Putin on Red Square during a military parade.

The extreme precautions to protect the leader’s health – Putin was 68 during the pandemic’s first year – ultimately narrowed his social circle. Russian technocrats who would’ve been against war had less contact with Putin than hardliners, Russian analysts have said.

One US intelligence report circulated to more than a dozen agencies in early 2022 cited a source who relayed that Putin’s behavior had become “highly concerning and unpredictable,” CNN reported at the time.

Today, Putin is certainly no longer as isolated as he was during the pandemic, but he remains difficult to decipher even for the countries closest in proximity to the Kremlin.

Ukrainian intelligence assessments of Putin in recent years have been bolder – sometimes beyond belief – than those of their US and European counterparts. Lt. Gen. Kyrylo Budanov, Ukraine’s top spy, has claimed that Putin has multiple body doubles who often appear in public instead of the actual president. Budanov has also questioned if the “real Putin” is still alive.

As the war has dragged into a fourth year, Putin’s determination to conquer Ukraine has arguably only intensified – making him an even more challenging interlocutor to come to an agreement with than in the past, said US officials and experts.

“By now he believes that if Russia doesn’t win this war, he won’t be in office anymore,” said Angela Stent, a former national intelligence officer for Russia at the State Department and a leading expert on post-Soviet Russia. “So there has been a change in the way that he views the West and his determination to push back, but I think the fundamental beliefs probably haven’t changed.”

That determination has made Europeans increasingly concerned about Trump getting lured into a deal that only rewards Russia for the invasion.

Zelensky warned this week that Putin will try to deceive Trump when they meet. The Ukrainian president said on Monday that his intelligence agencies reported that Putin “is definitely not preparing for a ceasefire or an end to the war.”

“Putin is determined only to present a meeting with America as his personal victory and then continue acting exactly as before, applying the same pressure on Ukraine as before,” Zelensky said in a post on X.

Last week, Witkoff left European allies “confused and uneasy” after Europeans were told he discussed Russian control over Ukrainians territories in exchange for a ceasefire, a European diplomat said.

But Trump appeared to agree on a call with Europeans ahead of the Putin summit that Ukrainian territory is not for him to negotiate – it is for Zelensky, European diplomats said. Still, analysts said that Trump administration officials’ focus on territorial exchange indicates that they still might be missing Putin’s greater aims.

“Putin is much more ideological today than he was in his earlier years,” said Michael McFaul, a former US ambassador to Russia. “He is not a transactional leader, as many in the West had often assumed in the past, but is more motivated by imperial ideas.”

“A person with that mindset is hard to negotiate with,” McFaul added.