A federal judge sharply questioned the Trump administration Monday about its decision to rush three planes carrying Venezuelan nationals out of U.S. airspace under President Donald Trump’s unprecedented invocation of wartime deportation powers against a criminal gang.

James Boasberg, the chief judge of the federal district court in Washington, was clearly galled by the government’s actions and legal arguments in the case, particularly its assertion that an order he issued Saturday to turn around any planes carrying such deportees had no force once they were outside U.S. territorial waters.

Only minutes before the hearing Monday, the Justice Department took the unusual step of asking a federal appeals court to remove Boasberg from the case altogether. The appeals court did not immediately act on that request.

At the heart of the issue is Trump’s invocation of the Alien Enemies Act, a 1798 statute intended to bolster the president’s ability to deport foreign nationals from countries with which the United States is at war. Trump issued a proclamation labeling Tren de Aragua, a Venezuelan criminal organization, as sufficiently linked to the Venezuelan government to trigger those wartime powers.

Boasberg on Saturday ordered the administration to refrain from removing anyone from the country under Trump’s claimed authority after five Venezuelans who feared deportation under the Alien Enemies Act filed suit. Those five men apparently remain in the country, in U.S. custody. But planes carrying about 250 other Venezuelan nationals — many of whom the Trump administration accused of being members of Tren de Aragua — departed from the U.S. shortly before Boasberg issued his order. They landed Saturday night in El Salvador, which had agreed to take the prisoners for a fee.

Then, Boasberg scheduled another court hearing on Monday evening to address claims from immigrant rights advocates that the Trump administration appeared to be defying the court.

At moments during the 45-minute hearing, the normally unflappable judge raised his voice, rejecting the Justice Department’s contention that the government had an exceptionally urgent need to move the planes.

Boasberg implied that the government had intentionally hurried the planes off the ground on Saturday afternoon because the government knew he had scheduled a hearing at 5 p.m. Saturday. “Any plane that you put into the air in or around that time, you knew that I was having a hearing at 5,” the judge said with evident frustration.

Boasberg also grilled a Justice Department lawyer over a key stretch of time on Saturday between two orders Boasberg issued. In the first order — which Boasberg issued orally from the bench — the judge directed the government to “immediately” turn around any planes carrying deportees subject to Trump’s proclamation. About 40 minutes later, Boasberg followed up with a written order in the court’s electronic docket that lacked some of the detail in his oral directive.

Deputy Associate Attorney General Abhishek Kambli claimed Monday that the government was free to ignore the oral order.

“We believe that there was no order given” orally, Kambli said. “An injunction is not ordered until it’s in the written filing.”

Boasberg, an appointee of President Barack Obama, was highly dubious.

“That’s a heck of a stretch,” the judge said. “You can’t violate the injunction. If you don’t like it, you can appeal it or seek to modify it.”

Boasberg also rejected the Justice Department’s claim that he lacked any authority over the flights once they cleared U.S. airspace.

“It’s not a question that the plane was or was not in United States airspace,” the judge said, adding that the power of federal courts does not “lapse at the water’s edge” or “the airspace’s edge.”

But Kambli said the foreign policy concerns related to the operation were paramount.

“These arrangements were the result of intensive and delicate negotiations between the United States and El Salvador,” he said.

DOJ further frustrated Boasberg by refusing to provide almost any details about the deportation operation, repeatedly invoking national security to defend the secrecy.

“Why are you showing up today and not having answers to why you can’t even disclose it to me?” the judge asked.

As the hearing neared its conclusion, Boasberg demanded that the government answer — by noon tomorrow — a series of questions about the flights and their passengers, as well as exactly when Trump signed the proclamation calling for the alleged gang members to be expelled from the country. He also ordered the filing of more briefs on the legal arguments in the case.

And Boasberg told the government lawyers that, just to be clear, he’d write down everything he wanted them to address.

“My oral orders don’t seem to carry much weight,” the judge said.