Judge Brian Murphy found the White House violated a court order with a deportation flight bound for the chaotic African nation carrying people from other countries who had been convicted of crimes in the U.S. He said those immigrants must get a real chance to raise any fears that being sent there could put them in danger.

The federal government argued that Murphy has stalled its efforts to carry out deportations of migrants who can’t be returned to their home countries. Finding countries willing to take them is a “a delicate diplomatic endeavor” and the court requirements are a major setback, Solicitor General D. John Sauer wrote in an emergency appeal asking the court to immediately halt his order.

Murphy, for his part, said he had given the Trump administration “remarkable flexibility with minimal oversight” in the case and emphasized the numerous times he attempted to work with the government, according to an order published Monday night.