A federal judge has invalidated Donald Trump’s punitive executive order targeting law firm Perkins Coie, ruling it as a violation of constitutional protections for free speech and due process. U.S. District Judge Beryl Howell’s decision marks the first legal assessment of Trump’s directives aimed at law firms involved in legal challenges against him or his allies. The ruling prevents federal agencies from enforcing Trump’s order against Perkins Coie, following a previous temporary restraining order issued by Judge Howell.

The Justice Department has the option to appeal this decision to the U.S. Court of Appeals for the District of Columbia Circuit. Perkins Coie, a prominent 1,200-lawyer firm, had been representing Hillary Clinton’s 2016 presidential campaign. Trump’s executive order sought to restrict the firm’s lawyers from government access and threatened to cancel federal contracts of its clients, leading Perkins Coie to challenge it as a violation of First Amendment free speech and Fifth Amendment due process rights.

This ruling represents a significant setback for Trump’s efforts to pressure law firms he accuses of using the justice system against him. Other major law firms have also challenged similar executive orders, with some reaching agreements with Trump to avoid punitive actions. The targeting of law firms has sparked criticism within the legal industry, with accusations of presidential coercion. Perkins Coie argued it was singled out over its work for Clinton’s campaign and diversity initiatives. The firms contesting the orders view them as existential threats that limit legal practice and intimidate clients.