But Boasberg has been on a mission to find out whether the Trump administration defied an oral order the judge gave that evening that also directed authorities to return any passengers on the two flights to the United States. The judge demanded specific details about the flights that shipped migrants detained in the U.S. to a Salvadoran prison.

On Monday night, the DOJ escalated its standoff with the judge by invoking the state secrets privilege, saying it could not provide further information about the flights because it was too sensitive to divulge. It involved negotiations with multiple foreign countries about deportations of alleged members of the transnational gang Tren de Aragua, the attorneys said. Disclosing the flight details to a judge, even in a nonpublic setting, would be a “breach of the trust on which our foreign relationships are based,” the attorneys said.

Boasberg has floated holding Trump officials in contempt, a penalty that could come with fines or jail time as a consequence of noncompliance. He has given the American Civil Liberties Union, which initiated the lawsuit about the Alien Enemies Act, until March 31 to submit a counterargument to the court. The judge could reach a conclusion on the compliance matter soon thereafter. The DOJ’s submissions to the court on Monday and Tuesday were part of that fact-finding process.

“The government’s not being terribly cooperative at this point, but I will get to the bottom of whether they violated my order,” Boasberg said at a hearing last week.

The ACLU’s lawsuit alleged that federal authorities gave the deportees no due process before flying them to a prison in El Salvador that abuses its detainees. The ACLU alleged that the Alien Enemies Act proclamation was not being implemented properly and that the administration mistakenly deported people who were not members of the gang.

The Trump administration has asked an appellate court to reverse Boasberg’s temporary restraining order. A three-judge panel heard oral arguments in the case on Monday and is expected to issue a decision soon.

In terms of Boasberg’s pursuit of information about flights that he believes violated his oral order, the judge may not be fully receptive to the Trump administration’s invocation of the state secrets privilege.

TRUMP DOJ WAGES DUAL FIGHTS IN VENEZUELAN MIGRANTS CASE

He observed last week that the DOJ had raised the privilege as a possibility at the eleventh hour after never mentioning that the information was even classified, let alone protected by a privilege so strong that it allows the government to withhold information from a judge.

The DOJ argues that Boasberg’s oral order, issued less than an hour before his written one on March 15, was too imprecise to have been binding.