A federal judge overseeing the criminal case that accuses Donald Trump of mishandling classified documents has signaled an openness to the former U.S. president’s defense claims, in a sign that prosecutors might face a difficult road ahead.

U.S. District Judge Aileen Cannon, who was nominated to the bench by Trump, has asked Trump and prosecutors to propose jury instructions based on two legal scenarios that favor a claim from Trump that national security lawyers said have little relevance to the charges.

Trump and Special Counsel Jack Smith, who brought the case, face a Tuesday deadline to respond to the judge’s order.

The dispute is another instance of Cannon lending credence to Trump’s legal arguments about highly sensitive records taken to his Mar-a-Lago estate in Florida when he left the White House in 2021.