Over the past several decades, the pressure has mounted on presidential children as the first-day-of-school ritual has become increasingly scrutinized. President Jimmy Carter’s choice to send his daughter, Amy, to Washington public schools triggered a media circus. The decision by President Bill Clinton and Hillary Clinton to send their daughter, Chelsea, to the private Sidwell Friends School in Washington made national news.

The Obamas’ decision to send their daughters, Sasha and Malia, to the same school in 2009 was also met with intense national interest. When both girls were shuttled to their first day of school by their mother, Michelle Obama, and a team of Secret Service agents, a photographer for Mr. Obama’s transition team captured the proceedings.

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Tiffany Trump, the president’s youngest daughter, in April. She started law school at Georgetown University last week.

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Al Drago/The New York Times

There was no such photo op on Tuesday. Barron’s privacy has been fiercely guarded by the Trump White House, where officials have taken pains to keep life normal and protect him from those critical of his family. In January, a writer for “Saturday Night Live” was suspended after she mocked the president’s son on Twitter.

When a writer for the conservative Daily Caller wrote that the 11-year-old should dress more appropriately in late August, the column drew widespread condemnation from the news media, the White House and a former first child who was once the subject of such criticism: Chelsea Clinton.

The exchanged spurred a rare moment of bipartisanship — on Twitter, least — between Mrs. Trump and Ms. Clinton, the daughter of Mr. Trump’s opponent.

Kate Andersen Brower, the author of the book “First Women,” said the high level of scrutiny directed at Barron, who unlike previous first children did not grow up with a father in politics, could be a factor in the Trump family’s decision to buck tradition. They skipped elite, progressive-leaning schools like Sidwell Friends and instead chose to send their son to a school farther from the White House.

In Maryland, Ms. Andersen Brower said, Barron might get some needed breathing room and distance from Washington, a heavily Democratic city where emotions over the outcome of the election still run high.

“Sidwell was very happy to have the Obama daughters,” Ms. Andersen Brower said. “This was a much more fraught situation.”

In May, Melania Trump, the first lady, released a statement that said the family had chosen for Barron to attend the school because of its “diverse community” and “commitment to academic excellence.” The coed school, which sits on a 19-acre campus, has a median class size of 15 and six students for each teacher. Tuition is $38,590 for middle school and $40,650 for high school, not including a $1,000 enrollment fee.

Georgetown University’s law school tuition is $59,850 a year. In the case of Tiffany Trump, a photo posted to her Instagram account was the only public clue she had arrived in Washington for school. Students there have been quietly wondering for months what Ms. Trump’s presence might mean for security on campus.

Students have probably noticed a difference in recent days. When both of the Trump children show up on their campuses, they bring with them much more than school supplies: the highly trained, earpiece-wearing and hardly school-age special agents of the Secret Service. The agency’s black S.U.V.s have toted all recent first children to and from school, and then followed them through the door.

That is where it gets complicated, said Mr. Basham and Mr. Sullivan, the former Secret Service directors.

“There is no playbook you can go by,” Mr. Basham said. “Of course, recognizing the consequences of something potentially happening is obviously extremely concerning, but it can be an incredibly boring assignment. It’s very challenging to keep yourself alert and focused day after day, sitting at school, waiting for the bell to ring — but they do.”

Mr. Sullivan, who led the Secret Service when the Obama daughters attended Sidwell Friends, said the agency did everything it could to attract as little attention as possible on campus. The hope, he said, is that the novelty of a presidential child and government agents passing in the hallway fades over time.

“You do everything you can to help them blend in as much as possible,” Mr. Sullivan said. “It gets a lot of attention at first, but after a while, people are going to focused on their own lives.”

Outside of St. Andrew’s on Tuesday, the flow of parents and students toward the red brick school buildings was uninterrupted. Save for a noticeable contingent of police officers in squad cars and on motorcycles, there was no sign of disorder. A single news van was camped outside.

The Trump children are not the only students in the area with Secret Service details: Back in Washington, school also began at Sidwell Friends, where Sasha Obama is a junior. The Obamas have said they will remain based in the capital at least until she graduates.

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