President Trump Donald John TrumpBiden on Trump's refusal to commit to peaceful transfer of power: 'What country are we in?' Romney: 'Unthinkable and unacceptable' to not commit to peaceful transition of power Two Louisville police officers shot amid Breonna Taylor grand jury protests MORE on Monday will hold his highly anticipated summit with Russian President Vladimir Putin, a meeting he has pursued despite warnings from advisers and allies — and the specter of the investigations into Moscow's election interference in 2016.

Trump has long wanted a closer relationship with Putin, something he believes can mend frayed ties between their two countries. But beyond his apparent affinity for Putin, many in Washington have questioned why the president is sitting down with his Russian counterpart and what he seeks to accomplish.

Here are five things to watch for when Trump and Putin meet in Helsinki:

Election interference

Russia’s interference in the 2016 election, already at the front of observers’ minds, has rocketed to the top of the agenda ahead of Monday’s summit.

Deputy Attorney General Rod Rosenstein Rod RosensteinDOJ kept investigators from completing probe of Trump ties to Russia: report Five takeaways from final Senate Intel Russia report FBI officials hid copies of Russia probe documents fearing Trump interference: book MORE announced Friday the indictment of 12 Russian intelligence officers who allegedly hacked into the Democratic National Committee and other Democratic groups. The announcement comes just days before the Helsinki summit, ramping up pressure on Trump to raise the issue with Putin.

But the president has long wavered on the matter, despite the U.S. intelligence community’s assessment that Russia interfered in the election. Just last month, Trump tweeted that “Russia continues to say they had nothing to do with Meddling in our Election!”

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Trump has repeatedly highlighted that denial — which Putin made during their first face-to-face meeting at last year’s group of Group of 20 summit — as a way of downplaying the issue.

“President Trump is now the outlier in his own administration, seemingly,” said a former Trump transition official.

The president has promised multiple times to press Putin on election interference, saying Friday he would “absolutely firmly ask the question” when they meet.

Trump has expressed a belief, however, there is not much he can do to deter their activity.

“I don’t think you’ll have any ‘Gee, I did it, I did it, you got me.’ There won’t be a Perry Mason here,” Trump said at a press conference with British Prime Minister Theresa May.

National security figures with ties to the White House hope Trump publicly warns Putin against interfering in the midterms and threatens the Russian leader with consequences.

But the worst-case scenario they fear is Trump remaining silent on the issue and raising the possibility of lifting sanctions on Moscow, something that would fuel criticism from political opponents who believe he is too close to Putin.

Democrats in Congress have called on Trump to cancel the summit entirely in response to the indictment, but there is no sign Trump is interested in doing so.

Syria

Trump has reportedly been eying a deal with Putin in Syria that is aimed at moving Iranian forces away from the border with Israel in exchange for withdrawing U.S. troops.

But both U.S. and Russian officials have been reluctant to give ground on thorny issues such as troop levels or territory, and experts are not optimistic a deal will be made in Helsinki.

“To me, this whole issue of expecting the Russians or hoping the Russians are going to deliver Iranian concessions in Syria is the triumph of blind hope over grim analysis,” said Robert Ford, former U.S. ambassador to Syria under former President Obama.

Under the terms of a possible deal, Russia would promise to limit Iranian presence near Syria’s border with Israel and Jordan and, in turn, the U.S. would allow Syrian President Bashar Assad’s forces to take control of the area.

U.S. forces have an outpost in southern Syria near the border with Jordan and Iraq known as al Tanf, which Pentagon officials have said is key to ensuring Iran does not complete the Tehran-to-Beirut land bridge it desires. But under the reported deal, U.S. forces would leave al Tanf — and eventually Syria — altogether.

Experts have warned Trump not to repeat the mistakes of his summit with North Korean leader Kim Jong Un, when he did not come away with an ironclad plan for denuclearization.

“If he buys a vague promise, then it looks like the Singapore summit where he gets some nice words without details from the other side of the summit table,” said Ford.

Crimea

Crimea has been at the heart of U.S.-Russia tensions since 2014. That’s when Russia annexed the peninsula off Ukraine, sparking a wave of international sanctions and other measures aimed at isolating Moscow.

But Trump has repeatedly left the door open to recognizing Russia’s claim over Crimea during his meeting with Putin, even repeating Moscow’s talking point that it has a rightful claim to the territory because most residents speak Russian.

The president stoked further concern this week when he again did not rule out the possibility during his press conference at the end of the tumultuous NATO summit.

“That’s an interesting question, because long before I got here President Obama allowed that to happen, that was under his watch, not my watch,” Trump said. “What will happen with Crimea from this point on? That, I can’t tell you.”

One of the post-Crimea punishments for Russia was getting booted from the then-Group of Eight world economic powers. But last month, on his way to the Group of Seven summit in Canada, Trump said that should be reversed.

“Russia should be in this meeting,” he said at the time. "Why are we having a meeting without Russia being in the meeting?"

The U.S. and its European allies stepped up their military posture and exercises in Eastern Europe after the Crimea annexation. But after Trump unilaterally agreed to cancel joint military exercises with South Korea during his summit with North Korea’s Kim, allies are fearful of him doing the same with Putin.

Republicans in Congress are cautioning Trump against a repeat performance.

“I think the president should listen to his security council and our secretary of Defense and our NATO allies on anything of substance dealing with the U.S. military posture. We’ve got to be careful, we’ve got to be strong,” said Sen. Richard Shelby Richard Craig ShelbySenate GOP eyes early exit Dems discussing government funding bill into February GOP short of votes on Trump's controversial Fed pick MORE (R-Ala.), who recently led a congressional delegation to Russia.

Arms control

Trump has said one of his top priorities for the summit is arms control, a topic that could produce a rare opportunity for the U.S. and Russia to find common ground.

Arms control advocates say Trump can score an easy win with Putin by agreeing to extend the New START Treaty for another five years. The treaty, negotiated by the Obama administration, caps the U.S. and Russia’s deployed nuclear warheads to 1,550 each and comes up for renewal in 2021.

“[Renewal] would ensure that we do not return to a numerical arms race,” said Thomas Countryman, former assistant secretary of State on international security and nonproliferation.

But most experts do not believe a decision on New START will come at the summit. Trump has dismissed the treaty as one of Obama’s “bad deals,” and it could take some convincing to get him on board.

Republicans have argued the treaty should not be extended while Russia is in violation of a separate arms control agreement known as the Intermediate-Range Nuclear Forces (INF) Treaty. That agreement, which has been credited with helping end the Cold War, bans ground-launched ballistic and cruise missiles with ranges between 500 and 5,500 kilometers.

The United States has repeatedly accused Russia of violating the INF Treaty by developing and deploying a banned missile, a charge Moscow denies.

The summit could provide an opportunity for Trump to address the INF violation directly with Putin, but experts say Russia has shown little appetite for reversing course.

Stagecraft

Even more than contentious policy issues, the visuals could be the most memorable part of the Trump-Putin summit.

Trump and Putin will hold a joint press conference, which should be a spectacle in and of itself and give U.S. media a chance to rare opportunity to press the Russian leader on election meddling and other key issues.

It could cause problems for Trump if he appears too friendly with Putin, especially given the timing of the meeting, just days after the hacking indictments.

But Trump’s desire to form a close bond with Putin could lead the president to give his Russian counterpart a warm reception, just like he did with Kim in Singapore.

It could fuel criticism back home that Trump has a greater affinity for strongmen than he does for longtime U.S. allies.

Days before the summit, Trump was shown grimacing during a group photo with NATO partners in Brussels and rolled his eyes when he was asked during a meeting with British Prime Minister Theresa May about critical comments he made about the U.K. leader.

Putin, a former KGB officer with a flair for the dramatic, could also have some tricks up his sleeve.

The Russian leader frequently shows up late for meetings with world leaders, even forcing Pope Francis to wait for 50 minutes before a 2015 sit-down in Vatican City.

Putin even brought his pet Labrador to a 2007 meeting with German Chancellor Angela Merkel, who has a well-known fear of dogs.

The Russian president later said he did not mean to scare Merkel and claimed he apologized after learning she is scared of dogs.