The Massachusetts Air National Guardsman charged with leaking a trove of military secrets was twice admonished by his superiors last year over "concerning actions" he took with regards to classified information, federal prosecutors said in a court filing on Wednesday.
Jack Teixeira was told by superiors in September and October "to no longer take notes in any form on classified intelligence information" and to "cease-and-desist on any deep dives into classified intelligence information," prosecutors wrote in the filing.
But even after being warned, a superior in February found Teixeira viewing classified materials that were not related to his primary duties, according to a Feb. 4 Air Force memo cited by prosecutors.
Wednesday's filing -- which argues in support of keeping Teixeira behind bars until his trial -- gives further insight into what prosecutors are learning in their investigation of Teixeira's actions leading up to his arrest last month as the alleged source of the massive leak of classified national defense information that has since spread across the internet.
Prosecutors wrote Wednesday that, in January, Teixeira had boasted about the vast amount of classified information he had access to -- writing "theres gonna be a f--- ton of information here . . .," according to one message obtained from the online platform Discord, where Teixeira frequently posted.
Another message, prosecutors argued, made clear Teixeira's "palpable" desire to continue to "obtain and disclose classified information." According to the Wednesday filing, he once wrote, "Man, how f----- up is it i can type out all this s--- and still be ready for more but can barely get through a two page college paper."
And not long after being warned by superiors, he acknowledged online what he was doing, writing in December that he was "breaking a ton of [unauthorized disclosure] regs" but "Idgaf what they say I can or can't share," according to prosecutors' motion.
His pattern of behavior showed "he will be undeterred by any restrictions this Court places upon him and will not hesitate to circumvent those restrictions if he deems it in his interest to do so," prosecutors contended.
"It is clear that the dissemination of the classified national defense information that the Defendant unlawfully posted was even more widespread and diverse than previously known," prosecutors wrote. "It is also clear that the Defendant publicly exalted in the breadth and sensitivity of the information that he was disclosing."
A native of Dighton, Massachusetts, Teixeira has been charged with unauthorized retention and transmission of national defense information as well as willful retention of classified documents, which collectively carry a maximum of 15 years in prison. He has not yet entered a plea.
He was arrested by the FBI on April 13 and is set to appear in court on Friday afternoon when a judge is expected to determine if he should remain detained.
The government's motion on Wednesday includes several memos that show Air Force officials documenting, in real time over a period of months, their problems with Teixeira's conduct regarding classified information. But it appears the Air Force did nothing to limit his access to such secrets.
One memo dated Sept. 15 states that an official "was made aware that A1C Jack Teixeira of the 102 ISS had been observed taking notes on classified intelligence information ... [and] put the note into his pocket."
"A1C Teixeira has been instructed to no longer take notes in any form on classified intelligence information," the memo continued.
A second memo, from Oct. 27, stated that "Teixeira was potentially ignoring the cease-and-desist order on deep diving into intelligence information given on 15 Sep 22."
That memo indicated Teixeira was instructed to "continue to cease-and-desist on any deep dives into classified intelligence information and focus on his job as 1D." (The Air Force has said Teixeira worked in Cyber Transport Systems.)
Portions of the September and October memos are redacted, so it is unclear if Teixeira was disciplined in either instance, but he "was offered the opportunity to explore cross training..." and declined the opportunity.
A third memorandum, on Feb. 4, documented that on Jan. 30, Teixeira was observed on a "JWICS" machine, which refers to a secure Joint Worldwide Intelligence Communications System, "viewing content that was not related to his primary duty and was related to the intelligence field."
Teixeira's defense team, for its part, has filed a motion in support of his pre-trial release citing prior cases involving people charged with various offense related to classified information who were permitted to be conditionally released before their trials.
Teixeira's public attorney, Allen Franco, has argued that even if the judge finds that he poses a risk of flight or obstruction, he should still be permitted to remain out of pretrial detention in the custody of his father or confined to a home with the presence of either his father, mother, stepfather, Air Force personnel or his lawyers.
Franco has suggested that Teixeira could have restrictions imposed on him such as location monitoring, barring him from accessing the internet or contacting any potential witnesses in the case and bond that could be secured by both his parents' homes.
Franco also argued that the government has offered "no evidence" that his client ever intended for information shared within the Discord server "to be widely disseminated."
Teixeira's father testified at an April court hearing that he was prepared to serve as a third-party custodian should his son be released. But on Wednesday, prosecutors wrote that such an arrangement couldn't "reasonably" satisfy Teixeira's continued appearance at trial or the public's safety.
Prosecutors and the defense have also advanced competing versions of Teixeira's character. Franco, his lawyer, has pushed back in court papers against the government's detailing of Texeira's suspension during his sophomore year in high school over allegations he made violent and racist threats.
The incident "was thoroughly investigated" at the time, Franco wrote, and Teixeira was allowed to return to school after a "handful" of days following a psychiatric evaluation.
Teixeira's lawyer disputed that he'd be a flight risk by pointing to how, when Teixeira became aware of his impending arrest, he sat on his mother's porch and read a Bible as he waited for law enforcement to arrive. (Teixeira also wore a long rosary necklace to a late-April court hearing.)
In Wednesday's filing, however, prosecutors wrote their ongoing investigation had found evidence that "belies the Defendant's efforts to minimize his criminal conduct and undercuts the Defendant's claim that he can be trusted to adhere to conditions of release imposed by the Court."
Prosecutors dismissed the defense's "narrative" about Teixeira's character.
"Among the conduct that could be contrasted with what the defense alleged to be the Defendant's peaceful reading of the Bible prior to his arrest is a recent video that has now been publicly published by The Washington Post," prosecutors wrote. "That video depicts the Defendant using racial and ethnic slurs while firing at a target, 'emptying the magazine of bullets' and ending his statement with 'I mag dump.'"
Prosecutors further pointed to what they called "the significant volume of racist, antisemitic, and violent rhetoric [Teixeira] posted online."
In sum, they wrote, Teixeira's "true nature" is "one of self-serving deceit."
ABC News' Trevor Ault and Christopher Donato contributed to this report.