BOSTON >> Superiors of the Massachusetts Air National Guard member charged with leaking highly classified military documents had raised concerns internally on multiple occasions about his handling or viewing of classified information, according to a court filing Wednesday.

Justice Department lawyers made the disclosure in court papers urging a magistrate judge to keep Jack Teixeira behind bars while he awaits trial in the case stemming from the most consequential intelligence leak in years. The judge is expected to hear more arguments Friday on prosecutors’ detention request and issue a ruling.

Teixeira is accused of sharing highly classified documents about top national security issues in a chatroom on Discord, a social media platform that started as a hangout for gamers. He has not yet entered a plea.

Prosecutors told the judge in their filing that Teixeira continued leaking documents even after he was admonished by superiors on two separate occasions last year over “concerning actions” he took related to classified information.

A September memo from the Air National Guard 102nd Intelligence Wing that prosecutors filed in court says Teixeira had been observed taking notes on classified intelligence information and putting the notes in his pocket. Teixeira was instructed at the time to no longer take notes in any form on classified intelligence information, the memo says.

Another memo from late October says a superior had been made aware that Teixeira was “potentially ignoring the cease-and-desist order on deep diving into intelligence information” given to him the month before. The memo says Teixeira attended a meeting and proceeded to ask “very specific questions.” He was told again to focus on his job, not any “deep dives” into classified intelligence information.

Still, a third memo from February says Teixeira was again observed viewing information “that was not related to his primary duty and was related to the intelligence field.” Teixeira “had previously been notified to focus on his own career duties and to not seek out intelligence products,” the memo said.

“The Defendant even continued to share information with his online associates, defying these admonishments and taking further efforts to conceal his unlawful conduct,” prosecutors wrote.

The revelations have raised questions about why military officials did not take further action and why Teixeira continued to have access to classified information after his superiors raised concerns.

Pentagon spokesperson Sabrina Singh was questioned today about why Teixeira’s leaders did not take action after the concerns were raised. Singh referred to the Justice Department and Air Force investigations and said those concerns and potential lack of response to them was one of the areas the inquiries would examine.

Lawyers for Teixeira, who was arrested last month on charges under the Espionage Act, are urging the judge to release Teixeira to his father’s home, noting that the man didn’t flee when media outlets began publishing his name shortly before his April 13 arrest. His lawyer told the judge last month that Teixeira “will answer the charges” and “will be judged by his fellow citizens.”

In their own court filing Wednesday, Teixeira’s lawyers noted there have been many Espionage Act cases in which courts have approved release or the government did not seek to keep the person behind bars pretrial. They have also said there is no allegation that Teixeira ever intended for documents to be distributed widely.

But prosecutors said in their filing Wednesday that one of the servers on the social media platform he posted classified information to had at least 150 users at the time the information was shared and “now may have many more users that are actively seeking access to information.”

“Among the individuals with whom the Defendant shared government information are a number of individuals who represented that they resided in other countries and who logged on to the social media platform using foreign IP addresses,” prosecutors wrote.

In messages, Teixeira bragged about the scope of information he had access to, writing, “The information I give here is less than half of what’s available,” prosecutors said. He also acknowledged he wasn’t supposed to be sharing the information, prosecutors said, writing in another message, “All of the s—- I’ve told you guys I’m not supposed to,” according to the Justice Department’s filing.

Magistrate Judge David Hennessy heard arguments from lawyers over detention late last month, but has yet to issue a ruling and scheduled a second hearing on the matter for Friday. In earlier court records, prosecutors revealed that Teixeira kept an arsenal of weapons before his arrest and has a history of violent and disturbing remarks.

The leaked documents appear to detail U.S. and NATO aid to Ukraine and U.S. intelligence assessments regarding U.S. allies that could strain ties with those nations. Some show real-time details from February and March of Ukraine’s and Russia’s battlefield positions and precise numbers of battlefield gear lost and newly flowing into Ukraine from its allies.