A federal judge in Washington edged closer Thursday to holding the Trump administration in contempt for possibly having violated his ruling pausing the deportation of scores of Venezuelans under a rarely invoked wartime statute.

In a sternly written order, the judge, James E. Boasberg, told the administration to explain to him by Tuesday why officials had not violated his instructions when they allowed two flights of immigrants to continue on to El Salvador even after he directed the planes to return to the United States.

Boasberg also called out efforts by the Justice Department to repeatedly stonewall his attempts to get information about the timing of the flights over the weekend.

“The government again evaded its obligations,” he wrote, adding that the Justice Department’s most recent filing about the flights was “woefully insufficient.”

Boasberg’s three-page order was a remarkable display of frustration with an administration that has sought not only to use the extraordinary powers of the wartime law, the Alien Enemies Act, to pursue its immigration agenda, but has also stubbornly refused to provide even the most basic information about the deportation flights.

In the past few days alone, Justice Department lawyers made a last-minute effort to cancel a hearing before Boasberg in which they were expected to discuss the flights in court. They then took the highly unusual step of asking the federal appeals court sitting over him to remove him from the case altogether.

All of this has unfolded as leading officials, including Attorney General Pam Bondi, and legions of President Donald Trump’s supporters have assailed Boasberg as a hack, a Marxist and a terrorist sympathizer. Trump himself has also entered the fray, demanding this week that Boasberg be impeached.

That prompted a rare public rebuke from Chief Justice John Roberts, who released a statement Tuesday saying that the appeals process, not impeachment, was the proper way to deal with unfavorable rulings.

The Trump administration, in several cases filed against it in the past two months, has faced accusations of having failed to comply with judges’ orders, but none of the proceedings so far has resulted in a finding of contempt. If a judge did find officials in contempt, it could lead to financial penalties or even, if the offense was serious enough, to the jailing of administration officials.

Constitutional crisis fears

But in the end, judges have little actual authority to enforce their orders in the face of disobedience. And legal scholars have expressed concern that if a judge eventually accuses the White House of disobeying an order and the administration presses forward anyhow, it could lead to a constitutional crisis.

Boasberg, the chief judge in U.S. District Court in Washington, has been trying for days, and in various ways, to get the administration to tell him — under seal, if needed — what time the two planes carrying the Venezuelan immigrants departed the United States, what time they left American airspace and what time they landed.

He originally instructed the Justice Department to provide him with that data by noon Wednesday. He then extended the deadline by another day after department lawyers asked for more time as they considered whether to invoke a rare doctrine called the state secrets privilege in an effort to get out of turning over the information.

On Thursday, the government finally filed court papers under seal to Boasberg, but hours later, he revealed in his order that the papers “repeated the same general information about the flights” that department lawyers had already given him in previous court filings and hearings.

Ultimatums

Appearing to reach the end of his patience, Boasberg, who has a reputation for being a measured and understated jurist, gave the government a series of ultimatums.

He told the administration to submit a sworn declaration by Friday at 10 a.m. from someone “with direct involvement in the Cabinet-level discussions regarding invocation of the state secrets privilege.” He also instructed the Justice Department to tell him by Tuesday if the administration intended to actually invoke the state secrets privilege.

The conflict over the flight data was only one of the disputes roiling the case, which has emerged in recent days as a flashpoint over the administration’s attempts to expand presidential powers and to question the ability of judges to challenge the decisions of the executive branch.

The Justice Department is also seeking in two separate courts to reverse Boasberg’s initial order pausing the deportation flights under the Alien Enemies Act. Department lawyers will appear in court Friday in front of Boasberg and Monday in front of an appeals court to debate the issue with lawyers for some of the Venezuelan immigrants.