Two major law firms asked separate judges Wednesday to permanently block President Donald Trump’s executive orders that were meant to punish them and harm their business operations.

The firms — Perkins Coie and WilmerHale — say the orders are unconstitutional assaults on the legal profession threaten their relationships with clients and retaliate against them based on their past legal representations or their association with particular attorneys whom Trump perceives as his adversaries.

Courts last month temporarily halted enforcement of key provisions of both orders, but the firms asked in court Wednesday for the edicts to be struck down in their entirety and for judges to issue rulings in their favor. Another firm, Jenner & Block, is scheduled to make similar arguments next week and a fourth, Susman Godfrey, is set to make its case next month.

“The entire executive order is retaliatory,” Dane Butswinkas, a lawyer who presented arguments on behalf of Perkins Coie, told a judge.

U.S. District Judge Beryl Howell did not immediately rule on the firm’s request, but she repeatedly expressed deep unease over the executive order, signaling that she was inclined to side with Perkins Coie.

She grilled a Justice Department lawyer over the government’s plans to suspend the security clearances of lawyers at the firm and asked him to respond to the suggestion that the blacklisting of disfavored law firms was similar to the “Red Scare” panic over communism decades ago. And she pressed him to explain why the Trump administration was forcing firms to disavow the use of diversity, equity and inclusion considerations in their hiring practices.

The spate of executive orders taking aim at some of the country’s most elite and prominent law firms are part of a wide-ranging retribution campaign by Trump designed to reshape civil society and extract concessions from powerful institutions. The actions have forced targeted entities, whether law firms or universities, to decide whether to push back and risk further incurring the administration’s ire or to agree to concessions in hopes of averting sanctions. Some firms have challenged the orders in court, but others have proactively reached settlements.

The executive actions have generally imposed the same sanctions against the law firms, including ordering that security clearances of attorneys be suspended, that federal contracts be terminated and that lawyers be barred from accessing federal buildings.