Just hours after the Supreme Court struck down President Trump’s original roster of punishing global tariffs, he defiantly proclaimed that he would stop at nothing to somehow bring them back. Seven months later, the work to revive those duties is well underway. But their return has landed the administration back in the same federal courthouse in New York where its legal troubles first began.

The latest phase of Mr. Trump’s ever-evolving trade war rests in the familiar hands of a panel of federal judges, who on Wednesday heard the third major case in less than two years challenging the president’s ability to tax imports from around the world. This time, the legal wrangling concerned the use of Section 301 of the Trade Act of 1974, which allows the administration to investigate unfair trade practices and impose tariffs if it finds that American businesses were harmed. In July, the government relied on the statute to impose tariffs on 86 countries at once.

The expansive nature of the tariffs prompted state officials and small businesses to file a series of lawsuits. Over roughly two hours on Wednesday, the Justice Department vigorously contested those claims, setting the stage for another high stakes decision from the Court of International Trade in downtown Manhattan. In an ominous sign for the Trump administration, the three-judge panel sounded skeptical throughout the proceedings that the administration had fulfilled the requirements of Section 301.

Judges on that specialized circuit have twice ruled against the president in major tariff cases. Ryan Majerus, a partner at the law firm King & Spalding, cautioned that it was hard to predict how the judges will rule based on their questions alone. But, he said: “They seemed inclined to want to put some guardrails around how Section 301 is invoked.”