By PHILIP MARCELO, Associated Press

NEW YORK (AP) — Lawyers for Mahmoud Khalil on Friday asked a federal judge to order the release of the Columbia University protester from an immigration lockup, saying the Trump administration missed an appeal deadline.

In a letter to U.S. District Judge Michael Farbiarz in New Jersey, the lawyers said Khalil has satisfied all the court’s requirements, including posting a $1 bond, while the lawyers for the government missed a 9:30 a.m. deadline the judge set 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.

The lawyers also say the government has declined to provide information about plans for Khalil’s release and hasn’t shown any other grounds for his continued detainment other than the reasons Farbiarz has already dismissed.

“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.