NEW YORK – Attorneys representing Mahmoud Khalil have urged a federal judge on Friday to mandate his release from immigration detention, arguing the Trump administration failed to meet an appeal deadline.

Addressing U.S. District Judge Michael Farbiarz in New Jersey, the attorneys noted that Khalil has fulfilled all the court’s conditions, which includes posting a $1 bond, while government lawyers missed the 9:30 a.m. cutoff set by the judge on Wednesday.

In response to the letter, the judge gave the government until 1:30 p.m. Friday to formally reply to the request to free Khalil.

Furthermore, the attorneys claim the government has not provided information about Khalil’s release plans and has not justified any further reasons for his detention beyond those that Judge Farbiarz has already rejected.

“The deadline has come and gone and Mahmoud Khalil must be released immediately,” his lawyers said in a statement provided by the American Civil Liberties Union, which is among the groups representing him. “Anything further is an attempt to prolong his unconstitutional, arbitrary, and cruel detention.”

Lawyers and spokespeople for the Justice Department and Homeland Security didn’t immediately respond to emails seeking comment.

The Trump administration vowed Wednesday to appeal Farbiarz’s ruling, in which the judge determined that Khalil had shown his continued detention was causing irreparable harm to his career, his family and his free speech rights.

He previously ruled that expelling Khalil from the U.S. on those grounds was likely unconstitutional.

Khalil, a legal U.S. resident, was detained on March 8 at his apartment building in Manhattan over his participation in pro-Palestinian demonstrations.

His was the first arrest under President Donald Trump’s crackdown on students who joined campus protests against the war in Gaza.

U.S. Secretary of State Marco Rubio has said Khalil must be expelled from the country because his continued presence could harm American foreign policy.

Khalil’s lawyers say the Trump administration is simply trying to crack down on free speech.

Khalil isn’t accused of breaking any laws during the protests at Columbia. The international affairs graduate student served as a negotiator and spokesperson for student activists.

He wasn’t among the demonstrators arrested, but his prominence in news coverage and willingness to speak publicly made him a target of critics.

The Trump administration has argued that noncitizens who participate in such demonstrations should be expelled from the country as it considers their views antisemitic.