Sitting aside Egyptian President Abdel Fattah al-Sisi in the Oval Office earlier this year, he eschewed any public lectures on widespread jailing of dissidents and journalists.
And meeting with Chinese leader Xi Jinping at Mar-a-Lago in April, Trump declined to raise Beijing's crackdown on opponents of the government.
After those meetings, White House officials said Trump would not let differences over human rights impede upon his efforts to strike deals with autocrats and dictators.
That mandate doesn't appear to extend to Cuba.
Rolling back Obama-era regulations that made it easier for Americans to travel to the island nation 90 miles from Florida, Trump cited the island's dismal human rights record, arguing that any easement of restrictions on doing US business there would have to wait until political prisoners are freed and fair elections are held.
"This is the simple truth of the Castro regime," Trump said. "My administration will not hide from it, excuse it or glamorize it. And we will never, ever be blind to it. We know what's going on and we remember what happened."
Applauding the Cuban dissidents in the audience, some of whom were tortured by the Castro regime, Trump pledged to "expose" the Cuban dictatorship for its human rights abuses.
"The Castro regime has shipped arms to North Korea and fueled chaos in Venezuela. While imprisoning innocents, it has harbored cop killers, hijackers and terrorists. It has supported human trafficking, forced labor and exploitation all around the globe," he said.
Of the global wrongdoing, Trump forcefully added, "to the Castro regime... the harboring of criminals and fugitives will end. You have no choice. It will end."
It was Trump's most public statement yet calling on a foreign government to improve its human rights record, one that came with specific promises to cut off US cash flows that could support the communist regime in Havana.
To fulsome applause, Trump said the United States would not lift sanctions against the Cuban regime until "all political prisoners are freed, freedoms of assembly and expression are respected, all political parties are legalized and free and internationally supervised elections are scheduled."
The direct comments, and the stark difference to Trump's silence on other countries, show the President's selective approach to human rights, one that punishes some nations for their abuses while largely ignoring others', at least in public.
Trump's aides insist he considers human rights when dealing with all foreign leaders. But they acknowledge his stance differs from country to country.
"It's true that the President approaches the question of human rights in different ways depending on the relationship the United States has with a particular country," Michael Anton, a spokesman for the National Security Council, said Friday. "He takes a different tack depending on the nature of the relationship between the two countries, but his concern is consistent no matter what the country."
Saudi Arabia and Arab countries
US presidents have long balanced outspoken recriminations over human rights abuses with the need to do business with autocratic leaders who run countries that are important US security and trade partners.
Trump and his aides have acknowledged he places more value on areas of potential cooperation than on human rights, and the President proclaimed himself during his swing through the Middle East in May that he would not lecture foreign governments about their practices.
But that vow may only to extend toward nations where explicit US interests are at stake. Trump hopes to partner with Saudi Arabia and Egypt to combat security threats -- including the sale of billions of dollars in US-made military equipment.
During his appearances with King Salman in Riyadh last month, Trump avoided any explicit mention of the country's restrictions on political dissent or its treatment of women.
"We are not here to lecture -- we are not here to tell other people how to live, what to do, who to be, or how to worship," Trump said in a speech to Arab leaders.
During Trump's meeting with al-Sisi in April, officials said he did raise the case of an American prisoner, Aya Hijazi, who had been held captive in an Egyptian prison for three years. Two weeks later Hijazi was released. The White House said the episode reflected Trump's commitment to advancing human rights. But al-Sisi -- who Trump calls a friend -- retains a hardline stance against dissent and political expression.
Meanwhile, he's working with China to counter North Korean aggressions while also carefully managing a tense economic relationship.
Cuba has less to offer the United States, at least in gross economic terms. US farmers have pressed the administration to continue opening the trade relationship with the island, though the market is relatively small. Cuban officials have warned that the limited intelligence sharing between Havana and Washington may stall considering Trump's announcement.
Some see a double standard in Trump's selective focus on human rights abroad.
"The Cuban administration is a violator of human rights as much as some of the people who President Trump has praised and admired on his recent trip, such as the King of Saudi Arabia and the president of Egypt," said Peter Schechter, a Latin America specialist who most recently headed the Atlantic Council's Latin American center. "We should be advocating for human rights everywhere, but it does not mean we should be breaking relations."
White House officials acknowledged this week that Trump had insisted on scaling back Obama's Cuba policy in order to fulfill his campaign promises. He didn't make similar vows to hold other countries to account for their human rights abuses as a presidential candidate, partly because immigrants from places like Saudi Arabia and Egypt don't reflect as powerful a voting bloc in the United States.
Trump has told people that he was deeply moved by his visit to the Bay of Pigs Museum weeks before Election Day in October 2016, especially on the human rights angle to the Cuba issue.
"I'm humbled by this endorsement from true freedom fighters," Trump said. "You were fighting for the values of freedom and liberty that unite us all. The same values that are at stake in our election."