Russian President Vladimir Putin is heading into his long-awaited first in-person meeting with President Trump on Friday with a very clear agenda. High on his list of priorities: getting rid of US sanctions against Russia.

Russia despises the extensive network of US sanctions that plagues many of its officials and top firms and acts as a drag on its struggling economy. Now, to Moscow’s dismay, Congress is looking to pass yet another round of harsh sanctions against the country.

Putin is also likely to ask for the return of the Russian Embassy’s country houses outside Washington and New York, which the Obama administration confiscated in December in response to Russia’s interference in the 2016 presidential election.

Putin’s argument to Trump will basically run along these lines: If you can prevent or neuter the new sanctions legislation being considered in the House of Representatives, lift some of the current ones that are having a crippling effect on the Russian economy, and return the confiscated properties, it will ease the strained relationship between Washington and Moscow and lay the groundwork for Russian concessions.

But could Trump actually lift sanctions on Russia?

The short answer is that it depends on which sanctions Trump wants to lift. The US has different types of measures in place against Moscow, each motivated by a different kind of Russian misbehavior. Some of them are locked in place through legislation, making it virtually impossible for Trump to make any kind of unilateral attempt to discard them.

But some of the biggest sanctions on Russia are held in place by executive orders, meaning that they can be overturned by the White House without congressional approval. Furthermore, relinquishing control of the seized Russian properties in the US — which, according to at least one leak in May, the White House is seriously considering — is also within Trump’s power.

The question on those measures is not whether Trump can pull it off. It’s whether he’d be willing to endure withering criticism that he’s in Putin’s pocket if he were to do so.

There are all kinds of sanctions on Russia. Only some of them can be lifted easily.

Broadly speaking, there are three main categories of US sanctions against Russia. The first relates to Moscow’s sale of weapons to countries that Washington wants to isolate in the global arena, such as North Korea. The second group of sanctions has to do with Russia’s various human rights violations, such as in the Chechnyan prison system. And the third category is related to Putin’s backing of separatists in eastern Ukraine and annexation of the Ukrainian territory of Crimea.

These sanctions are all administered by the executive branch, but Trump’s power to do away with them varies. The measures put in place because of Russia’s weapons sales and human rights misdeeds were passed by Congress, which means Congress both regulates their implementation and is needed to overturn them.

They’re a lost cause for Trump if he’s looking for any quick action on lifting sanctions — because some members of Congress, including many in Trump’s own party, are much more hawkish toward Russia than Trump is and have even taken steps to try to hamstring Trump’s ability to lift sanctions on Russia. In June, the Senate passed a bill 98-2 that calls for a new, more expansive set of sanctions against Russian organizations and includes language that would limit the president’s ability to terminate ones that already exist.

But the situation is different with the sanctions tied to Moscow’s adventurism in Ukraine. Those ones were put in place through executive orders by President Obama and can be revoked with the stroke of a pen by Trump.

It’s a key imperative for Russia to find a way to have these sanctions lifted — they’re the harshest of all the American sanctions, imposing crippling penalties on Russia’s banks and oil companies as well as targeting Putin’s inner circle.

The Ukraine-related sanctions hit the hardest

Obama imposed the Ukraine-related measures in 2014 using a series of executive orders. They began by targeting officials who were involved in Crimea’s seizure and the violence in eastern Ukraine, and then escalated further, adding more of Putin’s political and business allies. Among those targeted: his chief of staff, Sergei Ivanov, and Arkady Rotenberg, Putin’s former judo partner and one of the most powerful businessmen in Russia.

Eventually the big guns came out when the US penalized some Russian oil and gas companies and banks. Those measures meant that, for example, Russian companies could no longer work with American companies on lucrative oil operations in the Arctic.

But the most damaging aspect of the sanctions has probably been that debt-heavy Russian banks lost the ability to borrow money from US banks, pushing them into a serious cash crunch, which in turn has had a ripple effect on the country’s economy.

This has been compounded by the fact that American allies in Europe and elsewhere have joined in on them as well. In 2015, Russia estimated that Western sanctions cost its economy more than $100 billion — by this point, it’s likely to have cost many billions more.

Putin undoubtedly will consider having these sanctions lifted to be the jackpot, and could be willing to come up with some creative solutions to the war in eastern Ukraine in order to secure that outcome.

But to the horror of the Kremlin, the Trump administration recently expanded the targets under the Ukraine-related sanctions. The Russians were so furious that they backed out of a meeting with US Undersecretary of State Tom Shannon in late June.

For Trump, who has long said he wants to improve ties with Russia, such a move doesn’t seem to make a whole lot of sense. So why did they do it?

Trump might be trying to preempt the Senate bill

Richard Nephew, a senior research scholar at Columbia University who formerly coordinated sanctions policy at the State Department under Obama, suggested that it may have been an attempt by the White House to slow the progress of new sanctions legislation in Congress by showing that they’re willing to get tough with Russia without any new measures.

The timing certainly seems to support this interpretation: The Trump administration unveiled the expanded designations on the Ukraine-related sanctions just days after the Senate passed the bill curbing Trump’s ability to lift sanctions.

Currently, that bill is being held up in the House due to a procedural debate over its constitutionality. Putin will almost certainly want Trump to lean on the House GOP to ensure the bill is either torpedoed or weakened dramatically — something Democrats believe he may already be doing.

The question is what costs Trump is willing to incur to make the pro-Russian turn — if any at all. He could return the diplomatic compounds to Putin, he could goad the House Republicans to drag their feet on the new sanctions bill, and he could lift some of the Ukraine-related sanctions.

But unless he gets something magnificent from Putin in return, he’s going to be more vulnerable than ever to charges that his associates colluded with Russia during the campaign and that he’s simply rewarding Russia for its help. He’d boost his critics who want more serious congressional investigations into his connections to Moscow. And, perhaps most importantly to Trump, he’d be excoriated for looking weak and outmaneuvered by a leader who is an effective strategist but clearly possesses less power than him.

The safe play for Trump would be to concede nothing to Putin on sanctions and be willing to set low expectations for his already beleaguered attempt at warming ties with Russia. But prudence isn’t his strong suit.