A federal judge on Monday questioned whether the Trump administration ignored his orders to turn around planes carrying deportees to El Salvador in possible violation of an decision he'd issued minutes before.

District Judge James E. Boasberg was incredulous over the administration's contentions that his verbal directions did not count, that only his written order needed to be followed, that it couldn't apply to flights outside the U.S. and that they could not answer his questions about the trips due to national security issues.

“That's one heck of a stretch, I think,” Boasberg replied, noting that the administration knew as the planes were departing that he was holding a hearing on whether to briefly halt deportations being made under a rarely used 18th century law invoked by President Donald Trump about an hour earlier.

“I’m just asking how you think my equitable powers do not attach to a plane that has departed the U.S., even if it’s in international airspace,” Boasberg added at another point.

Deputy Associate Attorney General Abhishek Kambli contended that only Boasberg’s short written order, issued about 45 minutes after he made the verbal demand, counted. It did not contain any demands to reverse planes, and Kambly added that it was too late to redirect two planes that had left the U.S. by that time.

“These are sensitive, operational tasks of national security,” Kambli said.

The hearing over what Boasberg called the “possible defiance” of his court order marked the latest step in a high-stakes legal fight that began when President Donald Trump invoked the 1798 wartime law to remove immigrants over the weekend. It was also an escalation in the battle over whether the Trump administration is flouting court orders that have blocked some of his aggressive moves in the opening weeks of his second term.

Earlier Monday, the White House insisted that it had not defied the judge’s order.

At a press briefing, White House press secretary Karoline Leavitt made clear that the swift deportation of suspected members of the Venezuelan gang Tren de Aragua fell within the president’s authority under the Alien Enemies Act, a 1798 law that has only been used three times previously in history, each one during a time of war. 

“The president used his authority under the Alien Enemies Act to deport foreign terrorists — Tren de Aragua is now a designated foreign terrorist organization,” Leavitt said, referencing the administration’s designation in February of eight international cartels as foreign terrorist organizations. 

Trump over the weekend announced he was invoking the Alien Enemies Act to speed up deportations of members of Tren de Aragua in the U.S. before Boasberg almost immediately issued a written ruling Saturday requiring the administration pause such deportations. 

On Sunday, however, the administration announced that more than 200 people it said are affiliated with Tren de Aragua had landed in El Salvador, where the administration worked out a deal for the migrants to be held. The leader of El Salvador posted videos of the migrants arriving. 

Leavitt argued that planes carrying the migrants had already taken off before the written ruling came out just before 7:30 p.m. Saturday, stressing that the administration is prepared to defend its actions in court Monday. 

“I'm prepared to provide it right now, all of the planes that were subject to the written order, the judge's written order, took off before the order was entered in the courtroom on Saturday, and the administration will, of course, be happily answering all of those questions that the judge poses in court later today,” Leavitt said. 

Leavitt previewed the Trump administration’s argument in court, saying there are “questions about whether a verbal order carries the same weight, as a legal order, as a written order.”

“And our lawyers are determined to ask and answer those questions,” she added. 

Meanwhile, two organizations — the American Civil Liberties Union and Democracy Forward — that originally sued over the White House’s use of the Alien Enemies Act asked the federal judge on Monday to force the administration, under oath, to explain its actions despite the court order.

Trump's invocation of the act could allow him to deport any noncitizen he says is associated with the gang, without offering proof or even publicly identifying them. The plaintiffs filed their suit on behalf of several Venezuelans in U.S. custody who feared they'd be falsely accused of being Tren de Aragua members and improperly removed from the country.

“There’s been a lot of talk about constitutional crisis, people throw that word around. I think we’re getting very close to it,” warned Lee Gelernt of the ACLU, the lead attorney for the plaintiffs, during the hearing. After the hearing, Gelernt said the ACLU would ask Boasberg to order all improperly deported people returned to the United States.

Boasberg said he'd record the proceedings and additional demands in writing. “I will memorialize this in a written order since apparently my oral orders don’t seem to carry much weight,” Boasberg said.

Kambli stressed that the government believes it is complying with Boasberg's order. It has said in writing it will not use Trump's invocation of the Alien Enemies Act to deport anyone if Boasberg's order is not overturned on appeal, a pledge Kambli made again verbally in court Monday. "None of this is necessary because we did comply with the court’s written order,” Kambli said.

Boasberg's temporary restraining order is only in effect for up to 14 days as he oversees the litigation over Trump's unprecedented use of the act, which is likely to raise new constitutional issues that can only ultimately be decided by the U.S. Supreme Court. He had scheduled a hearing Friday for further arguments, but the two organizations that filed the initial lawsuit, the ACLU and Democracy Forward, urged him to force the administration to explain in a declaration under oath what happened.