A toy maker sued Trump over tariffs and won. Its operations are still in tatters.

Tariffs on Chinese imports are down from stratospheric levels. Federal courts have ruled the duties were invalid in the first place. And trade deals could further ease import duties.

But on the ground, it is a different story. Crucial equipment has been disassembled, packed and trucked hundreds of miles on mountain roads only to be trucked back on short notice. Staff members are constantly re-evaluating a catalog of more than 2,000 toys and games, deciding which to keep producing and which to put on ice indefinitely. And the business recently had to raise prices.

“We’re moving at the speed of light here—flying the plane while fixing it," said Woldenberg, who runs the family business. Founded by his grandfather in 1916, it now comprises two companies, Learning Resources and hand2mind.

For weeks, Woldenberg and his roughly 500 employees—most at a suburban Chicago headquarters—have hastened to halt shipments, reroute cargo, raise prices and freeze expansion plans. The companies sued President Trump and other administration officials in federal court, winning a reprieve that is now under appeal and on hold. On Wednesday, the companies asked the Supreme Court to intervene in their favor.

Through it all, the most pressing questions are how to move toy production out of China, where to move it—and how to get tons of manufacturing equipment there in time to meet deadlines for end-of-the-year holidays.

“It’s almost like an evacuation," Woldenberg said. “We don’t have a place to make important items our reputation is built around."

Lining up new factories in another country is just the start. Heavy manufacturing-molds must be transported hundreds or thousands of miles by truck or ship and then reassembled. Quality-control processes and safety inspections must be re-created.

On Woldenberg’s list: Vietnam, India and Cambodia. One place he isn’t considering: the U.S. American injection-molding factories aren’t set up—or cost-effective—for the painting, assembly and labor-intensive finishing the toys need, he said.

Employees have hurried to halt shipments, reroute cargo, raise prices and freeze expansion plans.

Flatbed to Vietnam

Woldenberg’s production has been centered on China since the 1990s, when his companies started pairing up with contract manufacturers there. Factories compete vigorously for his companies’ relatively small batches, and have plenty of the unskilled but experienced workers needed to manually smooth, paint, assemble and package the products, he said.

After the tariffs of Trump’s first term, Woldenberg began exploring new manufacturing centers and moved production for about 15% of his products to Vietnam and India over nearly three years. Last year, the companies imported $65 million of products, about 60% from China.

When Trump won his second term in November, Woldenberg prepared for a trade war with China and drafted a plan to offset tariffs as high as 40%: Cut costs by 10% in every department. Rein in capital expenditures. Negotiate concessions from factories in China. (He said he got about 5% on average “after a lot of arguing.") Keep his own price increases under 10%.

Then, Trump slapped 145% tariffs on goods from China. Woldenberg threw out his plan. With tariffs at that level, he started planning to move production. That meant relocating the company’s 1,500 injection molds installed in Chinese factories, weighing what he estimated to be 1.5 million pounds combined.

But where?

The answer was clear for one of his top products: GeoSafari Jr. Kidnoculars—bright blue, green and yellow binoculars sold under the Educational Insights brand. Amazon alone has shipped more than 9,000 a month lately, pricing them just under $10 each, and ranking it No. 1 among nature exploration toys.

A factory near Hanoi already made some Kidnoculars. Woldenberg’s team ordered the 13 molds in China to be sent there. They filled a flatbed truck with bulky blocks of metal stacked on pallets and wrapped in plastic.

By May 1, the Kidnocular molds had arrived. Production began soon after. “That’s probably the single easiest product to move," Woldenberg said.

Cooper the STEM Robot, a newcomer to the Learning Resources lineup, proved trickier. The cheerful, blue-and-black programmable ball with alligator-clip hands has sensors to detect objects and light, and can wheel along a line drawn by a child. It sells for $79.99 online. Woldenberg’s team hasn’t found a place to build it, or other electronics, outside China.

“Once the inventory that we have is gone, I don’t know how we’re going to replenish it," he said.

Suing the president

Woldenberg doesn’t dodge publicity. Under President Barack Obama, he fought tougher lead-testing rules—and in recent weeks has campaigned on cable television to end Trump’s tariffs. His daughter, a company executive, posts TikToks explaining the pain of tariffs.

The companies sued in late April, challenging the tariffs on constitutional and other grounds.

“It’s not really our corporate personality to wait for the building to fall on our head," Woldenberg said. “No one’s going to save me. We are going to save ourselves."

In court, he argued that even the president’s emergency powers don’t let him impose such tariffs without legislation. The government said that losing the case would hurt trade negotiations and that Trump needed to maintain the tariffs to pursue delicate talks over border crossings, narcotics control and rebuilding U.S. manufacturing.

While the case wound through the courts, the tariff policy kept changing.

In mid-May, the U.S. and China reached a surprise deal, lowering the new U.S. tariffs on Chinese imports to 30% for 90 days.

Production in China for Woldenberg was back on, at least for a few weeks. His team moved quickly, turning around a truck about to cross China’s border with Vietnam, weighed down by heavy steel molds needed for making Sight Word Swat, the Sneaky, Snacky Squirrel Game and other games and toys. Aborting the shipment cost the company $13,000.

Two more trucks bearing company molds had already crossed the border. Woldenberg would have held off moving them had he known a deal was coming. Costs in Vietnam were running 10% to 30% higher than in China for many products, he said.

More good news arrived at the end of May. A federal judge ruled that the government couldn’t impose the tariffs on imports by Woldenberg’s companies. The government appealed within hours. Meanwhile, the tariffs remained in place.

For Woldenberg, the temporary deal with China and his initial court victory are promising but not enough. His team is heading to India and Vietnam in coming weeks to oversee new production lines, which take time to get up to speed. Some molds, including those for the Peeksville Hide & Cheep Chicken Coop, are en route to India by ship. The company just raised prices, averaging 5% to 10%.

Trump recently suggested on social media that tariffs on China would be 55%.

Tariff rates for Vietnam and India are scheduled to rise sharply in July—to 46% and 26%, respectively. Woldenberg says he can’t predict whether those will stick, rise or fall, but says he can’t afford to import from China if tariffs are 55%.

“We’re like a refugee from a war—if the higher ground we sought isn’t safe, we will load everything up in a donkey cart and move again," Woldenberg said. “It’s a really terrible way to run a business."

Write to Theo Francis at theo.francis@wsj.com