A timeline of the legal wrangling and deportation flights after Trump invoked the Alien Enemies Act

President Donald Trump’s invocation of an 18th-century wartime law to deport hundreds of immigrants, most of them Venezuelans, to a prison in El Salvador has led to a showdown with the judiciary.

It has involved a series of legal filings, White House announcements, court hearings, deportation flights and a mocking social media post from a Central American leader.

Here is a timeline of events surrounding the invocation of the Alien Enemies Act. All times are Eastern.

Saturday, March 15

—2:16 a.m.: Two legal advocacy groups, the ACLU and Democracy Forward, sue on behalf of five Venezuelans held in immigration detention who fear they will be falsely labeled members of the Venezuelan gang Tren de Aragua and deported under the 1798 law, which lawyers expect to be invoked soon.

—9:40 a.m.: Judge James E. Boasberg issues a temporary restraining order preventing the government from deporting the five plaintiffs. He schedules a 5 p.m. hearing on whether to expand it. The Trump administration appeals.

—About 4 p.m.: The White House posts the order invoking the Alien Enemies Act.

—5 p.m.: Boasberg convenes a hearing and asks Deputy Assistant Attorney General Drew Ensign if the government plans to deport anyone under Trump’s new proclamation “in the next 24 or 48 hours.” Ensign says he doesn't know. He asks for time to find out. The ACLU warns that planes are apparently about to depart. Boasberg gives Ensign about 40 minutes to find out and recesses the hearing at 5:22 pm.

—5:26 p.m.: An airplane with the tail number N278GX, believed by activists to be carrying deportees, leaves Harlingen, Texas, near the border with Mexico, according to the flight tracking website FlightAware.

—5:45 p.m.: A second plane, with the tail number N837VA and believed by activists to be carrying deportees, departs Harlingen.

—About 5:55 p.m.: Boasberg reconvenes the hearing. Ensign says he still has no specifics. The ACLU again warns that planes are leaving. Boasberg says he has to issue a new order to avoid anyone being immediately deported.

—Around 6:45 p.m.: Boasberg tells Ensign: “Inform your clients of this immediately, and that any plane containing these folks that is going to take off or is in the air needs to be returned to the United States.” The judge verbally issues his order, which stands for 14 days, and notes that immigrants protected by it will remain in U.S. custody.

—7:26 p.m.: Boasberg's written order is released.

—7:36 p.m.: The plane with the tail number N278GX lands in Honduras.

—7:37 p.m.: A plane with the tail number N630VA, believed by activists to be carrying deportees, departs Harlingen. Government lawyers later say this plane held no one deported under the newly invoked law.

—8:02 p.m. The plane with the tail number N837VA lands in El Salvador.

—9:46 p.m.: The plane with the tail number N630VA arrives in Honduras.

—10:41 p.m.: The plane with the tail number N278GX departs Honduras.

Sunday, March 16:

—12:05 a.m.: The plane with the tail number N278GX arrives in El Salvador.

—12:41 a.m.: The plane with the tail number N630VA leaves Honduras.

—1:03 a.m.: The plane with the tail number N630VA arrives in El Salvador.

—7:46 a.m.: El Salvador’s president, Nayib Bukele, tweets a New York Post headline saying Boasberg had ordered planes turned around. Bukele adds “Oopsie … Too late” and a laughing/crying emoji.

—8:13 a.m.: Bukele tweets footage of the deportees arriving and being processed into his country’s .

—8:39 a.m.: Secretary of State Marco Rubio posts Bukele’s tweet.

—9:29 a.m.: White House Communications director recirculates Bukele’s laughing post

Monday, March 17

—5 p.m.: A hearing begins over what Boasberg has called the “possible defiance” of his court order. Goverment lawyers tell Boasberg that his verbal directions did not count, only his written order needed to be followed, that it couldn’t apply to flights outside the U.S. and that they could not answer his questions about the trips due to national security issues. Boasberg calls the arguments "one heck of a stretch.” ACLU lawyer Lee Gelernt, the lead attorney for the plaintiffs, warns that “I think we're getting very close” to a constitutional crisis.

—About 12:30 p.m.: White House press secretary Karoline Leavitt tells reporters that about 261 people were deported on the flights, including 137 under the Alien Enemies Act.

Tuesday, March 18

—8:05 a.m.: Trump criticizes Boasberg on his social media platform, Truth Social. "This judge, like many of the Crooked Judges’ I am forced to appear before, should be IMPEACHED!!!”

—11:56 a.m.: Chief Justice issues a rare public statement rejecting calls to impeach judges. “For more than two centuries, it has been established that impeachment is not an appropriate response to disagreement concerning a judicial decision,” he writes. “The normal appellate review process exists for that purpose.”

—About midday: Boasberg orders the administration to provide more information on the first two flights, including what time the planes left U.S. airspace, what time they landed in foreign countries and what time people deported under the proclamation were transferred out of U.S. custody. He gives the administration until noon Wednesday to respond.

Wednesday, March 19

—About 8 a.m.: The Justice Department resists Boasberg's order in papers filed hours before the noon deadline, saying the court should end its “continued intrusions” into executive branch authority. Government lawyers call the judge's questions “grave encroachments on core aspects of absolute and unreviewable Executive Branch authority relating to national security, foreign relations and foreign policy.”

—About 10:30 a.m.: Boasberg pushes back against Justice Department request to suspend his order for more information, saying “Although their grounds for such request at first blush are not persuasive, the Court will extend the deadline for one more day.”

Thursday, March 20

—About 3 p.m.: Boasberg calls Trump administration's response “woefully insufficient” after asking why its failure to turn around did not violate his court order.

Friday, March 21

—About 10:30 a.m.: Department of Justice attorneys tell Boasberg in a court filing that administration officials are debating whether to invoke a “state secrets privilege” in response to his questions.

—About 3 p.m.: Boasberg vows in a hearing for a lawsuit challenging the deportations that he will get answers about whether the government defied his order to turn the planes around. “I will get to the bottom of whether they violated my order, who ordered this and what the consequences will be,” he said.

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Associated Press writer Tim Sullivan contributed to this report.