The Trump administration’s attempt at punishing so-called sanctuary cities suffered another blow on Friday.

A federal judge in Chicago issued an order that temporarily blocks the U.S. Department of Justice from withholding federal grant money from cities that refuse to comply with the administration’s tough new stance on immigration.

U.S. District Judge Harry Leinenweber ruled that the city could suffer “irreparable harm” by complying with the requirements.

“The harm to the City’s relationship with the immigrant community if it should accede to the conditions is irreparable,” Leinenweber wrote. “Once such trust is lost, it cannot be repaired through an award of money damages.”

Sessions announced in July that certain grants would only be awarded to cities if they allowed federal immigration authorities access to detention facilities and provided 48 hours notice before releasing an undocumented immigrant wanted by federal authorities.

Chicago, which has requested $2.2 million in federal money this year, asked for a temporary stop to Sessions’ requirements on Monday, arguing that it was an overreach of authority to withhold money from cities if they don’t comply with certain standards.

But the attorney defending the Department of Justice, Chad Readler, said that cities like Chicago had already accepted grants that required compliance with special conditions and that “The attorney general has final authority on all grants issued by the department.”