Trump has tweeted repeatedly in recent days in support of protesters who surged into the streets in anger over the apparently accidental downing of a Ukrainian jetliner and their government's initial attempt to conceal its role in the disaster.
But his encouragement carries a risk by seeming to confirm the claims of Iranian hard-liners who accuse the U.S. of fomenting the unrest.
"When the Iranian people are upset with their government for blatantly lying about shooting down a plane, he should have taken the high road and send his condolences to the families," said Jon Alterman, director of the Middle East Program at Center for Strategic and International Studies. "By seeming to make it about him, he de-legitimizes the protesters and allows the government to portray the protests as a U.S. plot."
Previous administrations have sought to keep some distance between Washington and demonstrators opposed to Iran's Islamic leadership. That was why the Obama administration offered only muted expressions of support during the major political unrest in Iran in 2009.
Trump and his team have no such qualms. They see their pro-demonstrator comments — even the president's tweets in Farsi on Sunday — as a way to further pressure Tehran.
Popular anger swelled Monday in Iran over the downing of the Ukrainian jet, which was apparently knocked out of the sky by an Iranian missile hours after the Islamic Republic fired a barrage of missiles at Iraqi bases housing American soldiers. Iran's action was in response to the U.S. killing of its top military leader, Gen. Qassem Soleimani, in a drone strike.
All 176 people on board the jet, including scores of young Iranians and people of Iranian descent, were killed, prompting widespread shock and outrage in Iran and around the world.
Ali Rabiei, a government spokesman, insisted Iran's civilian officials learned only on Friday that the Revolutionary Guard had shot down the plane. The Guard answers directly to Supreme Leader Ayatollah Ali Khamenei.
"The point is that we did not lie," Rabiei said. He went on to blame the U.S. for "spreading the shadow of war over Iran."
Ebrahim Raisi, the head of Iran's judiciary, issued a warning to protesters, saying "the agents of America and agents of foreign countries" want to use anger over Flight 752 to "compromise" Iran's security. Iran often blames anti-government protests on foreign conspiracies.
Yet others say the Trump administration's hands-on approach might not make any difference.
"The reality is when (President Barack) Obama offered only tepid support to Iranian protesters in 2009, the regime still called them American agents and crushed them. If the Trump administration offers more enthusiastic support, the regime will call them American agents and attempt to crush them," said Karim Sadjadpour, an Iran expert and senior fellow in the Middle East program at the Carnegie Endowment for International Peace.
"The best thing any U.S. administration can do is inhibit the regime's ability to shut down the internet and repress people in darkness," he said. "But, I think the Islamic Republic's penchant for repression is high regardless of whatever anyone says in D.C."
In a series of tweets sent since late last week as protests against Iran's shooting down of a Ukrainian passenger jet intensified, Trump has personally exhorted the Iranian people to rise up and be heard.
He has applauded the apparent refusal of some to walk over painted flags of Israel and the United States at a Tehran campus in a quiet show of defiance. He has also demanded that the government allow the protests and protect the demonstrators.
"To the leaders of Iran - DO NOT KILL YOUR PROTESTERS," he tweeted on Sunday. "Thousands have already been killed or imprisoned by you, and the World is watching. More importantly, the USA is watching. Turn your internet back on and let reporters roam free! Stop the killing of your great Iranian people!"
On Saturday, as protests grew following the admission by the Islamic Revolutionary Guard Corp that it had unintentionally shot down the Ukrainian plane, Trump tweeted, "To the brave, long-suffering people of Iran: I've stood with you since the beginning of my Presidency, and my Administration will continue to stand with you. We are following your protests closely, and are inspired by your courage."
Beyond supporting the protesters, Trump and fellow Republicans have denounced Democrats, saying they have not expressed robust backing for the Iranian demonstrators.
"Even under threat of tear gas or even gunfire, the brave people of Iran are themselves displaying more willingness to criticize their own brutal rulers than we saw in the initial responses from some Democrats and so-called experts right here at home," Senate Majority Leader Mitch McConnell, R-Ky., said Monday on the Senate floor.
Secretary of State Mike Pompeo also joined in, following an unprecedented appeal to the Iranian people last year to send in photos and videos of security forces cracking down on protests that erupted over fuel price increases that the government had blamed on U.S. sanctions.
"The United States is with them in their calls for freedom and justice, in their justified anger at the Ayatollah and his minions," Pompeo said in a speech at Stanford University on Monday. "And I repeat President Trump's insistence that Iran not harm a single protester. The world must do the same."
"The voice of the Iranian people is clear," Pompeo tweeted over the weekend. "They are fed up with the regime's lies, corruption, ineptitude, and brutality of the IRGC under @khmanei_ir's kleptocracy. We stand with the Iranian people who deserve a better future."