He once expressed hope that President Vladimir V. Putin of Russia would be “my new best friend,” but with friends like him, President Trump hardly needs enemies.

Russia’s armed seizure of three Ukrainian ships in the days before the two leaders are scheduled to meet on the sidelines of the Group of 20 meeting in Buenos Aires has threatened to upend Mr. Trump’s plans to forge a fruitful relationship with Mr. Putin and may deepen the renewed tension between the former Cold War rivals.

After two years of going out of his way to avoid public criticism of his Russian counterpart, Mr. Trump has inched closer to a breaking point, declaring that he was “not happy” about the confrontation in the Sea of Azov and suggesting that he might even call off his session with Mr. Putin scheduled for Saturday.

As of Wednesday, the Kremlin said it still expected the meeting to proceed and the White House did not indicate otherwise. But if the two leaders do get together, Mr. Trump will face pressure to more forcefully condemn Russian aggression or risk once again looking deferential to Mr. Putin as he did in Helsinki this summer when he seemed to accept the Russian’s word that he had not interfered in the 2016 presidential election.

“If President Trump is as forward leaning as he usually is with President Putin, that is obviously sending a signal that whatever happens in the Sea of Azov, we can move on,” said Angela E. Stent, a former national intelligence officer for Russia under President George W. Bush and author of the forthcoming book “Putin’s World.” “What the Russians want is a reaffirmation that however much we complain about that, the U.S. is not going to do anything.”

Despite the cascade of bipartisan criticism of his handling of the Helsinki encounter, Mr. Trump has been eager to meet again with Mr. Putin, but has never made clear exactly why.

No concrete agreements were announced in Helsinki and the two nations remain at odds not only over Russian aggression against Ukraine but also over the strife in Syria and the fate of the Intermediate-Range Nuclear Forces Treaty, or I.N.F., signed by Ronald Reagan and Mikhail Gorbachev in 1987.

No concrete agreements are expected in Buenos Aires either, and at a briefing this week, John R. Bolton, the president’s national security adviser, offered little illumination of the agenda beyond saying the two leaders would discuss “arms control issues” and “regional issues, including the Middle East.”

“I think it will be a continuation of their discussion in Helsinki,” he said.

In the months after Helsinki, Mr. Trump first suggested that Mr. Putin come to Washington, then the two talked about getting together earlier this month in Paris. Buenos Aires was the third choice, although Mr. Trump evidently still hopes to host Mr. Putin at the White House in the new year.

What no one anticipated was the naval standoff between Russia and Ukraine. Russian forces seized three small Ukrainian naval vessels and over 20 sailors, including at least three wounded in a shooting by the Russian side, and briefly blocked passage through the Kerch Strait. Ukraine’s government declared temporary martial law.

Some diplomats and analysts said it was not clear whether the clash was intended or the two sides stumbled into a confrontation. But either way, they said, Mr. Putin seemed likely to use it to test the boundaries of Mr. Trump’s professed friendship, which often appears at odds with the rest of his administration. Even as Mr. Trump sticks to warm words, his administration has imposed sanctions, kicked out diplomats, shipped weapons to Ukraine and threatened to scrap the I.N.F. treaty over Russian violations.

Mr. Trump, who first expressed his hope that Mr. Putin could be his “new best friend” as a businessman sponsoring a Miss Universe pageant in Moscow, has stuck to the same theme even as investigators examine whether his campaign conspired with Russia in 2016 when Mr. Trump was running against Hillary Clinton. He has denied any collusion despite a meeting held by his son, son-in-law and campaign chairman with Russians offering dirt on Mrs. Clinton on behalf of the Russian government.

Now it is the Ukraine standoff that is complicating his desire for a friendly get together. “Circumstances keep conspiring against him as has his own team, but he won’t let go of that idea,” said Andrew Weiss, a Russia specialist at the Carnegie Endowment for International Peace. “That’s central to his disruptive foreign policy agenda. It’s also important at a time when he’s looking at a long-term contentious relationship with China.”

Mr. Trump told reporters on Monday that he was upset about the naval clash in the Sea of Azov. “We do not like what’s happening either way,” he said. “And hopefully it will get straightened out.” But he did not directly blame Russia nor did he call on Moscow to release the ships and the sailors.

He went a little further in an interview with The Washington Post on Tuesday. “I don’t like that aggression. I don’t want that aggression at all. Absolutely,” Mr. Trump said, then tried to shift the burden to America’s allies. “And by the way, Europe shouldn’t like that aggression. And Germany shouldn’t like that aggression.”

Mr. Bolton has become the most critical driver of Russia policy, while the Defense and State Departments take a back seat, analysts said. Known as a Russia hawk in the past, Mr. Bolton lately has channeled the president. Asked about the Ukraine clash this week, Mr. Bolton offered no criticism, deferring to Nikki R. Haley, the departing ambassador to the United Nations, who previously condemned Russia’s “outlaw actions.”

Sarah Huckabee Sanders, the White House press secretary, would not say on Wednesday whether the meeting with Mr. Putin would be scrapped.

“The president is receiving regular briefings on the Russia-Ukraine situation from his national security team, including briefings Monday, Tuesday afternoon and again today,” she said in a statement. “We will keep you posted when there is additional public information or any policy announcements on this matter.”

But lawmakers have raised the temperature on the president, arguing that his approach has sent a signal that Mr. Putin can get away with whatever he wants. Without a more meaningful deterrence, they warned, Russia may effectively claim control of the Sea of Azov just as it annexed Crimea in 2014. A bipartisan group of senators introduced a resolution calling on Mr. Trump “to forcefully express opposition” to Russia’s aggression.

“Instead of giving Putin a free pass, President Trump should announce new sanctions against Russia, call for the immediate return of Ukrainian vessels and crewmen, and call off any planned meetings with Vladimir Putin at the upcoming G-20 summit,” said Senator Jack Reed, Democrat of Rhode Island.

Others said a meeting could still be useful, noting that presidents have met with leaders of hostile countries during times of tension if only to use the conversations to press for actions to defuse the tension. The question remains what Mr. Trump wants.

“You can make the argument that you should keep the dialogue going,” said Ms. Stent, who is now director of the Center for Eurasian, Russian and East European Studies at Georgetown University. “But we’re not seeing anything they would call deliverables from these meetings.”

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