The Trump administration has transferred hundreds of immigrants to El Salvador even as a federal judge issued an order temporarily barring the deportations targeting Venezuelan gang members under an 18th-century wartime declaration, officials said Sunday. Flights were in the air at the time of the ruling.

U.S. District Judge James E. Boasberg issued an order Saturday blocking the deportations, but lawyers told him there were already two planes with immigrants in the air — one headed for El Salvador, the other for Honduras. Boasberg verbally ordered the planes be turned around, but they apparently were not, and he did not include the directive in his written order.

“Oopsie … Too late,” Salvadoran President Nayib Bukele, a Trump ally who agreed to house about 300 immigrants for a year at a cost of $6 million in his country’s prisons, wrote on X above an article about Boasberg’s ruling. That post was recirculated by White House communications director Steven Cheung.

Secretary of State Marco Rubio, who negotiated an earlier deal with Bukele to house immigrants, posted on the site: “We sent over 250 alien enemy members of Tren de Aragua which El Salvador has agreed to hold in their very good jails at a fair price that will also save our taxpayer dollars.”

Steve Vladeck, a professor at the Georgetown University Law Center, said that Boasberg’s verbal directive to turn around the planes was not technically part of his final order but that the Trump administration violated the “spirit” of it.

“This just incentivizes future courts to be hyper specific in their orders and not give the government any wiggle room,” Vladeck said.

The immigrants were deported after Trump’s declaration of the Alien Enemies Act of 1798, which has been used only three times before in U.S. history.

The law, invoked during World Wars I and II and the War of 1812, requires a president to declare the United States is at war, giving him extraordinary powers to detain or remove foreigners who otherwise would have protections under immigration or criminal laws. It was last used to justify the detention of Japanese American civilians during World War II.

The ACLU, which filed the lawsuit that led to Boasberg’s temporary restraining order on deportations, said it was asking the government whether the removals to El Salvador were in defiance of the court.

“This morning, we asked the government to assure the Court that its order was not violated and are waiting to hear, as well as trying to do our own investigation,” ACLU’s lead lawyer, Lee Gelernt, said in a statement Sunday.

A Justice Department spokesperson Sunday referred back to an earlier statement from Attorney General Pam Bondi blasting Boasberg’s ruling and didn’t immediately answer questions about whether the administration ignored the court’s order.

Venezuela’s government in a statement Sunday rejected the use of Trump’s declaration of the law, characterizing it as evocative of “the darkest episodes in human history.”

Tren de Aragua originated in an infamously lawless prison in the central state of Aragua and accompanied an exodus of millions of Venezuelans, the overwhelming majority of whom were seeking better living conditions after their nation’s economy came undone last decade. Trump seized on the gang during his campaign to paint misleading pictures of communities that he contended were “taken over” by what were actually a handful of lawbreakers.

The Trump administration has not identified the immigrants deported, provided any evidence they are members of Tren de Aragua or that they committed any crimes in the U.S. It also sent two top members of the Salvadoran MS-13 gang to El Salvador who had been arrested in the U.S.

Video released by El Salvador’s government Sunday showed men exiting airplanes onto an airport tarmac lined by officers in riot gear. The men, who had with their hands and ankles shackled, struggled to walk as officers pushed their heads down to have them bend down at the waist.

The immigrants were taken to the notorious CECOT facility, the centerpiece of Bukele’s push to pacify his once violence-wracked country through tough police measures and limits on basic rights.

The Trump administration said the president signed the proclamation contending Tren de Aragua was invading the U.S. on Friday night but didn’t announce it until Saturday afternoon. Immigration lawyers said that, late Friday, they noticed Venezuelans who otherwise couldn’t be deported under immigration law being moved to Texas for deportation flights. They began to file lawsuits to halt the transfers.