For the past six months, prosecutors working for the special counsel Jack Smith have sought to determine whether former President Donald J. Trump obstructed the government’s efforts to retrieve a trove of classified documents he took from the White House.

More recently, investigators also appear to be pursuing a related question: whether Mr. Trump and some of his aides sought to interfere with the government’s attempt to obtain security camera footage from Mar-a-Lago that could shed light on how those documents were stored and who had access to them.

The search for answers on this second issue has taken investigators deep into the bowels of Mar-a-Lago, Mr. Trump’s private club and residence in Florida, as they pose questions to an expanding cast of low-level workers at the compound, according to people familiar with the matter. Some of the workers played a role in either securing boxes of material in a storage room at Mar-a-Lago or maintaining video footage from a security camera that was mounted outside the room.

Two weeks ago, the latest of these employees, an information technology worker named Yuscil Taveras, appeared before a grand jury in Washington, according to two people familiar with the matter.

Mr. Taveras was asked questions about his dealings with two other Trump employees: Walt Nauta, a longtime aide to Mr. Trump who served as one of his valets in the White House, and Carlos Deoliveira, described by one person familiar with the events as the head of maintenance at Mar-a-Lago.

Phone records show that Mr. Deoliveira called Mr. Taveras last summer, and prosecutors wanted to know why. The call caught the government’s attention because it was placed shortly after prosecutors issued a subpoena to Mr. Trump’s company, the Trump Organization, demanding the footage from the surveillance camera near the storage room.

The call also occurred just weeks after Mr. Deoliveira helped Mr. Nauta move boxes of documents into the storage room — the same room that Mr. Deoliveira at one point fitted with a lock. The movement of the boxes into the room took place at another key moment: on the day before prosecutors descended on Mar-a-Lago for a meeting with Mr. Trump’s lawyers intended to get him to comply with a demand to return all classified documents.

The Trump Organization ultimately turned over the surveillance tapes, but Mr. Smith’s prosecutors appear to be scrutinizing whether someone in Mr. Trump’s orbit tried to limit the amount of footage produced to the government.

They asked Mr. Taveras an open-ended question about if anyone had queried him about whether footage from the surveillance system could be deleted.

It remains unclear what investigators learned from questioning Mr. Taveras in front of the grand jury and whether they were able to make any headway in their efforts to determine if steps had been taken to interfere with the handing over of the surveillance tapes.

But the focus on the tapes is the latest effort by Mr. Smith to determine whether Mr. Trump or his aides engaged in any sort of obstructive behavior. Prosecutors are examining whether the former president has in effect been playing games with government officials in different agencies for more than a year — including the Justice Department, which issued a subpoena for all classified documents in Mr. Trump’s possession last May, and the National Archives, which sought to retrieve reams of presidential records from Mr. Trump that he held onto after leaving office, some of which included classified material.

There is no indication that Mr. Taveras is a subject of Mr. Smith’s investigation. His lawyer, Stanley Woodward Jr., declined to comment.

Mr. Deoliveira’s lawyer, John Irving, did not respond to a message seeking comment.

All three men — Mr. Taveras, Mr. Deoliveira and Mr. Nauta — have been questioned extensively by prosecutors over their roles in handling the boxes and the tapes. Mr. Trump’s aides maintain that nothing nefarious took place, and that activities that prosecutors are treating with suspicion were simply part of efforts to comply with the subpoenas or were routine conversations that happened without the participants knowing in some cases about the existence of the subpoenas issued by the Justice Department for the security footage and for the classified documents in Mr. Trump’s possession.

Nonetheless, one person briefed on the events said the interactions concerning the security tapes were enough to arouse suspicion among Mr. Smith’s investigators. Moreover, people briefed on witness interviews say, it has become clear that Mr. Smith views a number of people connected to Mr. Trump with skepticism.

Both Mr. Irving and the lawyer representing Mr. Nauta and Mr. Taveras, Mr. Woodward, are being paid by Mr. Trump’s political action committee, Save America, which itself has been under scrutiny by Mr. Smith’s team. Prosecutors are looking into whether the group raised money from donors by claiming it would be earmarked for legal challenges to the 2020 election, but that Mr. Trump’s aides knew he had lost.

The Washington Post reported on Tuesday about a conversation between an unnamed I.T. worker and an unnamed maintenance worker at Mar-a-Lago.

Mr. Taveras’s grand jury appearance was not the first time that Mr. Smith’s team has focused on the question of how the security tapes at Mar-a-Lago were handled. Prosecutors have also issued subpoenas to Matthew Calamari Sr. and his son, Matthew Calamari Jr., who have long overseen security issues for the Trump Organization.

The prosecutors have sent separate subpoenas to the company seeking surveillance footage from Mar-a-Lago, people with knowledge of the matter said. The first such subpoena was issued last June, and since then, prosecutors have sent several more subpoenas for a wider array of footage, one person with knowledge of the matter said.

The prosecutors appear to have sought the footage in order to get a clearer picture of the movement of the boxes of documents at Mar-a-Lago. But there were gaps in the footage, the person said, and the prosecutors have also been examining whether someone intentionally stopped the tape or if technological issues caused the gap.

The prosecutors have also subpoenaed a software company that handles all of the surveillance footage for the Trump Organization, including at Mar-a-Lago, The New York Times previously reported.

The attempts by Mr. Smith’s team to get to the bottom of what was happening with the boxes and the tapes reflect a fundamental challenge that prosecutors have faced since the start of the documents investigation: Mr. Trump’s post-presidential world at Mar-a-Lago is as much of a mishmash of loyalists and other officials as his chaotic White House was, and those who surround him most at his private club are employees with whom he has developed direct personal relationships over years.

Mr. Nauta was a military aide serving as a valet in the Trump White House, requiring a level of intimate proximity to the president that few staff members develop. After the Trump administration ended, Mr. Nauta retired from the military and went to work for Mr. Trump directly. And Mr. Deoliveira once parked cars at the club, a Trump aide said.

Before working on the information systems at Mar-a-Lago, Mr. Taveras managed them at the Trump International Hotel and Tower and at the Trump SoHo Hotel, according to his LinkedIn page.

Alan Feuer covers extremism and political violence. He joined The Times in 1999. @alanfeuer

Maggie Haberman is a senior political correspondent and the author of “Confidence Man: The Making of Donald Trump and the Breaking of America.” She was part of a team that won a Pulitzer Prize in 2018 for reporting on President Trump’s advisers and their connections to Russia. @maggieNYT

Ben Protess is an investigative reporter covering the federal government, law enforcement and various criminal investigations into former President Trump and his allies. @benprotess

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