A federal judge on Monday questioned whether the Trump administration ignored his orders to turn around planes carrying deportees to El Salvador, a possible violation of the 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 that had left the U.S. and that the administration could not answer his questions about the deportations 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 about to decide whether to briefly halt deportations being made under a rarely used 18th century law invoked by 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 Kambli 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.

“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 Monday 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.

On Saturday night, Boasberg ordered the administration not to deport anyone in its custody through the newly-invoked Alien Enemies Act, which has only been used three times before in U.S. history, all during congressionally declared wars. Trump issued a proclamation that the law was newly in effect due to what he claimed was an invasion by the Venezuelan gang Aragua Train.

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.

Told there were planes in the air headed to El Salvador, which has agreed to house deported migrants in a notorious prison, Boasberg said Saturday evening that he and the government needed to move fast. “You shall inform your clients of this immediately, and that any plane containing these folks that is going to take off or is in the air needs to be returned to the United States,” Boasberg told the government’s lawyer.

According to the filing, two planes that had taken off from Texas’ detention facility when the hearing started more than an hour earlier were in the air at that point, and they apparently continued to El Salvador. A third plane apparently took off after the hearing and Boasberg’s written order was formally published at 7:26 p.m. Eastern time. Kambli said that plane held no one deported under the Alien Enemies Act.

El Salvador’s President, Nayib Bukele, on Sunday morning tweeted, “Oopsie…too late” above an article referencing Boasberg’s order and announced that more than 200 deportees had arrived in his country. The White House communications director, Steven Cheung, reposted Bukele’s post with an admiring GIF.

Later Sunday, a widely circulated article in Axios said the administration decided to “defy” the order and quoted anonymous officials who said they concluded it didn’t extend to planes outside U.S. airspace. That drew a quick denial from White House press secretary Karoline Leavitt, who said in a statement “the administration did not ‘refuse to comply’ with a court order.”

The administration argues a federal judge does not have the authority to tell the president whether he can determine the country is being invaded under the act, or how to defend it.

After Boasberg scheduled a hearing Monday and said the government should be prepared to answer questions over its conduct, the Justice Department objected, saying it could not answer in a public forum because it involved “sensitive questions of national security, foreign relations, and coordination with foreign nations.” Boasberg denied the government’s request to cancel the hearing, which led the Trump administration to ask that the judge be taken off the case.

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.

As the courtroom drama built, so did international fallout over the deportations to El Salvador. Venezuela’s government on Monday characterized the transfer of migrants to El Salvador as “kidnappings” that it plans to challenge as “crimes against humanity” before the United Nations and other international organizations. It also accused Bukele’s government of profiting off the plights of Venezuelan migrants.

“President, I respectfully say to you, are you going to support this cruelty, this injustice … of imprisoning noble, hard-working migrants, good people, without trial, without having committed crimes in El Salvador, without any kind of sentence issued by a Salvadoran court?” President Nicolás Maduro said on state television. “Is this legal? Is it fair? Is it humane?”

Trump’s proclamation alleges Tren de Aragua is acting as a “hybrid criminal state” in partnership with Venezuela.

Families of some Venezuelans in U.S. custody scrambled to find out if their loved ones had been sent to El Salvador. Multiple immigration lawyers said they had clients who were not gang members who were being moved for possible deportation late Friday.

Franco Caraballo was held by immigration authorities during a routine check-in Feb. 3. His immigration lawyer, Martin Rosenow, said Caraballo not been accused of a crime. Caraballo’s wife believes he’s been wrongfully accused of belonging to the gang because of a tattoo he got marking his daughter’s birthday,

He called his wife Friday night in a panic because he was being handcuffed and put on a plane to an unknown destination in Texas, from where flights to El Salvador departed.

That was the last the family heard of him and he’s disappeared from the federal immigration detainee locator system. “I’ve never seen anything like this,” said Rosenow.

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Cano reported from Caracas, Venezuela. Joshua Goodman in Miami, Michael Kunzelman in Washington, D.C., and Nicholas Riccardi in Denver contributed to this report.