Federal judge Paul Friedman seemed skeptical of the new press policy implemented by the Pentagon last week, calling aspects of it “weird” and Kafkaesque.

Friedman struck down key aspects of the previously implemented Pentagon media policy on 20 March, but at the latest hearing on Monday stopped short of ruling on a motion filed by the New York Times to force compliance of his decision.

Friedman was particularly skeptical about the ways in which press space was being provided to the seven New York Times reporters, whom he previously ruled should have their press access badges returned.

The Times, along with dozens of other news organizations, chose not to sign the new restrictions implemented by the Pentagon last fall and returned their long-held passes. The Times sued the Trump administration over the policy.

Julian Barnes, one of the Times reporters at issue, had attested that he was told that library space was available for the journalists to use while the Pentagon built out a new space on the Pentagon grounds for all credentialed media workers to use. But, he wrote in a statement, “the Pentagon Press Office staff indicated that they were unsure how we could access the library.”

“How weird is that?” Friedman, a district court judge, said on Monday. “Is it catch-22? Is it Kafka? What’s going on? That hardly seems consistent with right of access and the first amendment.” (Lawyers for the government responded that a decision had been made to allow the Times reporters to use a Pentagon shuttle to reach the library.)

Theodore J Boutrous Jr, a lawyer representing the Times, charged that the administration was “brazenly, blatantly flouting the court’s order” by announcing the closure of the press space known as Correspondents’ Corridor and by creating a new policy that requires journalists to be escorted around the building by a Pentagon staff member.

“Nothing will stop them,” he said. “Not a court order. Not an injunction.”

With the new requirement requiring escorts, Boutrous said Pentagon press credentials were now “worthless”.

“They’ve made the press credentials that we fought so hard to get back a meaningless piece of plastic,” he added. “They’ve violated the first amendment.”

As he had during a previous hearing, the judge expressed alarm that journalists could be penalized for asking questions of military officials, which he said they had the right to do – and that a Pentagon employee could simply decline to answer.

The new policy includes language stating that, by offering anonymity to a Pentagon employee, a journalist would be demonstrating knowledge that the employee was not authorized to disclose the information, thereby putting their press pass at risk.

But the judge seemed skeptical that a source using anonymity suggested that they were leaking classified information. “Aren’t there lots of reasons why people in government ask for anonymity?” he asked. “People ask for anonymity because they’re afraid of retribution” or “because their bosses won’t like it”, he said, suggesting that it could create a “chilling effect”.

Timothy Parlatore, who played a central role in designing the revamped press restrictions announced last fall, told reporters after the hearing that the new restrictions didn’t bar questions – but prevented journalists from trying to force reluctant staffers to reveal information after they had indicated they would not do so.

“What we’re talking about here are when they go to department employees and they say: ‘Hey, can you tell me about this?’ And the employee’s like: ‘No, I don’t want to talk to you.’ And they say: ‘Well, what if I give you anonymity? Will you talk to me then?’ Then they’re trying to get somebody to talk who’s already said that they don’t want to talk,” he said.

He also said that the Pentagon did not plan to go through articles and try to determine who the anonymous sources were – but would act if an employee conveyed that a reporter had asked them to disclose classified information, something that would be barred under the language of the new policy. “Anytime a person with a security clearance has somebody that approaches them to try to solicit that information, they’re supposed to report that,” he said.

Parlatore, asked about the judge’s invocation of the Joseph Heller novel Catch-22, said it was based on “creative misinterpretations by the New York Times lawyers” and “a fictional interpretation of the policy”.

The goal of the press policy, Parlatore said, was to reduce leaks of classified information. “There was a significant amount of leaks of classified information and that was something that the department has an obligation, a statutory obligation, to try to stop,” he said.

Parlatore claimed that the policy had already paid dividends in a decrease of leaked classified information.

At the end of the hearing, the judge asked a lawyer for the government, Sarah Welch, to submit – by the end of the day – a brief explaining the case law basis for creating a new press policy in response to a court order striking down the crux of the previous policy.

Amid the US war on Iran, “time is of the essence”, Boutrous, the Times lawyer, said. “There is a war going on and the American people are being shut down from information.”