A federal judge said Thursday that the Trump administration missed a court deadline to disclose details on deportation flights to El Salvador, escalating President Donald Trump’s ongoing legal battle with the judiciary.

U.S. District Judge James Boasberg said that the government’s lawyers failed to meet the deadline he set for them to submit information about the administration’s deportation flights, which included individuals who were targeted for immediate removal under the 1798 Alien Enemies Act, and whether they knowingly defied his court order.

In a blistering order sent Thursday evening, the judge noted that the government “again evaded its obligations” to submit information about the flights, even after he offered the opportunity for them to do so under seal. The filing they did submit was hours late and failed to answer his questions.

Instead, he said, the court was sent a six-paragraph declaration from a regional ICE office director in Harlingen, Texas, which notified the court that Cabinet secretaries are “actively considering whether to invoke the state secrets [act] privileges over the other facts requested by the Court’s order.”

WHO IS JAMES BOASBERG, THE US JUDGE AT THE CENTER OF TRUMP’S DEPORTATION EFFORTS?

President Donald Trump is seen in a side-by-side split photo with U.S. District Judge James Boasberg for the U.S. District Court of Columbia.

President Donald Trump, left, and U.S. District Judge James Boasberg. (Associated Press/Getty Images)

“This,” he said, “is woefully insufficient.”

Boasberg on Saturday had granted an emergency restraining order blocking the Trump administration from using the 1798 law to deport Venezuelan nationals, including alleged members of the gang Tren de Aragua, for a period of 14 days. He also ordered any flights in the air to return to U.S. soil immediately.

Hours later, however, a plane carrying hundreds of U.S. migrants, including Venezuelan nationals removed under the law in question, arrived in El Salvador. 

Split of President Donald Trump and U.S. District Judge James Boasberg

President Donald Trump and U.S. District Judge James Boasberg. (Getty Images)

Boasberg immediately ordered the government to submit more information to the court, as part of a “fact-finding hearing” to determine whether the Trump administration knowingly defied his order, and how many individuals were deported.

After the government repeatedly failed to comply, citing national security issues, he told them they could do so under seal by noon Thursday. 

Boasberg had asked government lawyers to submit information on how many planes departed the U.S. on Saturday carrying people deported “solely on the basis” of that proclamation, how many individuals were on each plane, where the planes landed, what time each plane took off from the U.S. and from where.

Pam Bondi looks on while Trump speaks at her swearing in ceremony

President Donald Trump, accompanied by Pam Bondi, speaks before Bondi is sworn in as Attorney General in the Oval Office of the White House in Washington, D.C., on Feb. 5. (Andrew Harnik/Getty Images)

“To begin, the Government cannot proffer a regional ICE official to attest to Cabinet-level discussions of the state-secrets privilege; indeed, his declaration on that point, not surprisingly, is based solely on his unsubstantiated ‘understand[ing],'” he said.

Boasberg then ordered the Trump administration to submit a brief by March 25 explaining why it did not violate his order by failing to return the individuals in question on the two earliest planes that arrived from El Salvador to the U.S. on March 15.

“By March 21, 2025, at 10:00 a.m., Defendants shall submit a sworn declaration by a person with direct involvement in the Cabinet-level discussions regarding invocation of the state-secrets privilege,” he added.  

Boasberg had previously warned the Trump administration of consequences if it were to violate his order. 

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Still, at least one plane with deported migrants touched down later that evening in El Salvador. “Oopsie, too late,” Salvador President Nayib Bukele said in a post on X. 

In the days since, government lawyers have refused to share information in court about the deportation flights, and whether the plane (or planes) of migrants knowingly departed U.S. soil after the judge ordered them not to do so, citing national security protections. 

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