(CNN) — The Trump administration’s aggressive and fast-paced effort to advance its immigration agenda has exposed existing challenges with a dated system and raised concerns that authorities are flouting due process to ram deportations through.

Since taking office, President Donald Trump and his team have taken extraordinary measures to crack down on immigration, including invoking a rarely used wartime authority, known as the Alien Enemies Act of 1798, that has pitted the administration against a federal judge and prompted public backlash.

Meanwhile, the Trump administration has made multiple missteps in recent weeks, including mistakenly deporting a Salvadoran man whose case will be heard in a federal courtroom on Friday. The errors kept happening despite federal agents assuring they are carefully vetting each person before putting them on flights to a notorious prison in El Salvador.

Trump’s border czar Tom Homan has repeatedly maintained that authorities have done due diligence to gather information that the migrants they are deporting should be removed, especially from the Latin American gangs MS-13 or Tren de Aragua.

After hundreds of alleged gang members were flown to El Salvador last month in possible violation of a judge’s order, Homan said in an interview with ABC that “every single” migrant was a member of one of the gangs “according to the information” given to him “from the field.”

“A lot of gang members don’t have criminal histories, like a lot of terrorists in this world,” Homan said. “We have to count on social media, we have to count on surveillance techniques, we have to count on sworn statements from other gang members.”

Multiple detainees on those flights were eventually returned to the US because the Salvadoran prison wouldn’t take them once they landed there.

In the court fight over the deportations using the Alien Enemies Act, a senior Immigration and Customs official, Robert Cerna, defended the process for identifying members of the Venezuelan criminal organization Tren de Aragua, or TdA.

“Agency personnel carefully vetted each individual alien to ensure they were in fact members of TdA,” Cerna wrote in a declaration. “Officers and agents well versed in gang activity in general and TdA in particular reviewed the information gathered on each alien, identifying TdA members based upon the results of investigative techniques and information.”

But Cerna also wrote the US has little specific information about the detainees it believes are Tren de Aragua gang members.

“The lack of specific information about each individual actually highlights the risk they pose. It demonstrates that they are terrorists with regard to whom we lack a complete profile,” the ICE official said in his declaration.

The immigration push made national headlines again this week, when the administration admitted it shouldn’t have deported Kilmar Armando Abrego Garcia, the Salvadoran national who was living in Maryland, to the notorious mega-prison in his home country, even though he had been granted a protected status that should have prevented him from being removed there.

White House press secretary Karoline Leavitt called the man’s removal a “clerical error.”

Also this week, a judge in Texas found that a man was wrongfully detained by immigration authorities, after he narrowly avoided being put on one of those deportation flights to El Salvador. The judge ordered the immediate release of Gil Rojas, a Venezuelan national whose attorneys had obtained a court order keeping him in the US just before the series of flights took off in mid-March.

Courts weigh in

The cases underscore the complexity of the US immigration system: Proceedings can take years, people are granted a variety of different legal statuses, and the process for both immigrants and the federal government is cumbersome.

The mid-March deportation flights to El Salvador were central to a court hearing on Thursday, where US District Judge James Boasberg considered whether government attorneys misled him about the flights and if they or others in the administration should be held in contempt.

Boasberg pressed for answers, sharply questioning the Justice Department about the administration’s rush to fly detainees to the Salvadoran prison on Saturday, March 15. The judge pointed out that in its haste, the administration risked putting people on the planes who shouldn’t have been.

The court fight – parts of which are before the Supreme Court – has raised questions about the reach of executive authority on immigration policy.

“The district court has no ability to – in any way – restrain the president’s authorities under the Alien Enemies Act, or, as I believe, to conduct the Foreign Affairs the United States,” Stephen Miller, Trump’s White House deputy chief of staff, told CNN’s Kasie Hunt on “The Arena” last month.

The American Civil Liberties Union attorneys are arguing that some of the migrants may have been sent to El Salvador erroneously because of common choices they made, like getting tattoos of a soccer ball and crown. One detainee said the tattoo was for the soccer team Real Madrid, but the administration read it as a possible sign of gang affiliation.

The case tests Trump’s power to send migrants away without removal proceedings where the migrants can argue they aren’t gang members. The high court hasn’t yet decided what it will do.

At an appeals court hearing last week, one of the judges said mistakes could be easily made with the administration’s current process.

“You all could have put me up on Saturday and thrown me on a plane thinking I’m a member of Tren de Auga and giving me no chance to protest,” DC Circuit Court of Appeals Judge Patricia Millett said. She added at the court hearing that in her hypothetical, she wouldn’t be able to argue, “‘Excuse me, no I’m not, I’d like a hearing.’”

Denying gang affiliation

While senior Trump officials have expressed confidence in their deportation decisions, migrants and their advocates say quick decisions have been catastrophic and may flout longstanding immigration procedures.

Immigration attorneys and family members have argued that some of the Venezuelans sent to El Salvador’s mega prison last month are not tied to gangs, like the administration has described. Some of those removed had also been in the middle of their immigration proceedings before being sent to another country.

Many are still seeking answers.

On Wednesday, attorney John Dutton attended an immigration hearing for his client, Henrry Albornoz Quintero, who Dutton believes was sent to El Salvador.

Asked by the immigration judge about the whereabouts of Albornoz Quintero, a Venezuelan national who was in immigration detention, the ICE attorney only stated he’s no longer in the agency’s custody.

The judge pressed for more information, calling the lack of answers ridiculous, according to Dutton. With no official confirmation of his deportation from ICE, another hearing has been scheduled.

Lindsay Toczylowski, co-founder and president of the Immigrant Defenders Law Center, also told CNN that her client, a Venezuelan asylum seeker, was abruptly removed to El Salvador before his immigration proceedings had concluded.

Toczylowski’s client was expected to appear virtually for his immigration hearing from ICE detention last month, but he wasn’t there. The ICE prosecutor didn’t have information, according to Toczylowski, and the judge rescheduled the hearing.

A few days later, ICE confirmed in immigration court that Toczylowski’s client had been among those sent to El Salvador.

Court documents have shed light on some of the confusion with the flights to El Salvador.

One Venezuelan woman who was being held in Texas was flown to El Salvador along with a handful of other female Venezuelan detainees. But they were sent back to the US after landing at the Salvadoran prison. El Salvador’s infamous Center for Terrorism Confinement, known as Cecot, wouldn’t take the women, according to the filings.

“All the men got off the plane,” the woman, who is only identified by the initials S.Z.F.R., wrote in a recent sworn statement in the case before Boasberg. “The remaining women asked what happens to us? I was told that the President of El Salvador would not accept women. I was also told that we were going back to detention in the US.”

Prison guards in El Salvador also refused a male detainee of Nicaraguan descent because that Central American county was outside the agreement the US struck with El Salvador.

“I overheard a Salvadoran official tell an ICE officer that the Salvadoran government would not detain someone from another Central American country because of the conflict it would cause,” the detainee wrote in a sworn statement.

The Trump administration conceded in a court filing Monday that it mistakenly deported Abrego Garcia, the Maryland father, to El Salvador “because of an administrative error” and argued it could not return him because he’s now in Salvadoran custody.

A lawsuit has been filed over his removal, and a hearing is scheduled on Friday.

Prior to his removal, he was arrested by ICE in mid-March “due to his prominent role in MS-13,” according to a court declaration from a senior ICE official. His attorneys say he’s not a member of the gang, nor does he have any ties to it.

“As others were removed from the flight for various reasons, he moved up the list and was assigned to the flight. The manifest did not indicate that Abrego Garcia should not be removed,” Cerna, an acting ICE field office director, said in his declaration.

CNN’s Alejandra Jaramillo and Devan Cole contributed to this report.

The-CNN-Wire
™ & © 2025 Cable News Network, Inc., a Warner Bros. Discovery Company. All rights reserved.