US lawmakers and federal investigators continue to look into Russia's election interference, along with possible collusion between Trump campaign associates and Russian government officials.
That puts Trump under intense scrutiny over how he handles the sit-down with Putin, a former Russian intelligence agent known to come to meetings like this well-prepared.
The White House has scheduled 35 minutes for the meeting, raising questions about how much ground the leaders can be expected to cover.
Trump, who likes to have neatly packaged achievements to pair with high-profile meetings, may seek some concessions from Russia to show he's delivering progress and helping restore a once-productive relationship that he recently described as being at an "all-time low."
Putin would almost certainly want something in return.The list of issues ranges from Syria to Iran to Ukraine, and now North Korea, following Pyongyang's test this week of a missile capable of striking the US.
Russia wants the US to return the two compounds in New York and Maryland that were seized by the Obama administration as punishment for election meddling.
It also wants the U.S. to ease sanctions it imposed on Russia after Putin annexed the Crimean Peninsula, and over Russia's support of separatist elements in Ukraine.
The US wants a resumption of adoptions of Russian children by American parents, which Russia banned in 2012, along with an end to what it claims is intensifying harassment of US diplomats and other officials stationed in Russia.Lawmakers in both political parties say Trump must confront Putin over the election.
Several senior Democratic US senators have served notice that Trump would be in "severe dereliction" of his presidential duty if he fails to confront Putin over the issue, telling Trump in a letter that he must make clear that Russia's interference in US democracy will not be tolerated.
"The upcoming elections cannot be a playground for President Putin," said Minority Leader Chuck Schumer of New York; Dick Durbin of Illinois, the Senate's No. 2 Democrat; and the top Democrats on the Intelligence, Armed Services, and Foreign Relations committees.
Adam Kinzinger, a member of the House Foreign Affairs Committee, said this week that he will "raise holy hell" if Trump goes soft on Putin.
"It is very important for us to make a statement that Russia does not meddle not just in our elections, here and the future, but in our allies,"' he said.
Every detail of the Trump-Putin meeting will be scrutinized, from their facial expressions to the color of their neckties to how they shake hands.
"I expect an Olympic-level of macho posturing between these two leaders," said Derek Chollet, executive vice president and senior adviser for security and defense policy at the German Marshall Fund, a Washington think tank.
"The big thing to watch will be what Putin asks for and what he offers in return and whether there's a sense of receptivity on the president's part."
Before Putin, Trump will try to manage another rocky international relationship when he meets with Mexican President Enrique Pena Nieto.
Pena Nieto had been scheduled to visit the White House shortly after Trump took office, but he scrapped the trip at the last minute due to disagreement with Trump over the US president's insistence that Mexico pay for the wall he has vowed to build along the US-Mexico border to deter illegal immigration. Pena Nieto insists Mexico will not pay.
Trump has vowed to tighten border security and crack down on undocumented workers and drug cartels, but he has been less firm on getting Mexico to pay for the wall.
He reassured Pena Nieto in April that he would not pull out of the North American Free Trade Agreement, which involves the US, Mexico and Canada. But Trump said he could still withdraw if he concludes that a renegotiated pact would not produce "a fair deal" for all sides.
The Putin meeting is the highlight of a hectic, four-day European visit for Trump, who addressed thousands of Poles in an outdoor speech in Warsaw, Poland.
He met in Germany with Chancellor Angela Merkel, the summit host, and had dinner with two Asian allies - Japanese Prime Minister Shinzo Abe and South Korean President Moon Jae-in - to discuss North Korea's aggression.
The Group of 20 gathering of the world's leading rich and developing nations is the first since Trump announced that the US would withdraw from the Paris climate agreement, deeply disappointing Merkel and other US allies who had hoped to maintain momentum in battling climate change. Even as Trump has said in vague terms he would like to renegotiate the Paris accord, European leaders have vowed to press forward.
- AP