Trump said trade deals would come easy. Japan is proving him wrong.

When Japanese officials arrived in Washington in late May, Lutnick and Greer warned them that if the two sides couldn’t work out an agreement soon, the conversations might start shifting from easing the tariffs President Trump had recently imposed toward additional punitive measures, according to people familiar with the matter. The Americans said they might demand a cap on the number of vehicles Japan could export to the U.S.—a policy known as a voluntary export restriction.

But the Japanese officials stood their ground. From the start, they had told the Americans they wouldn’t agree to any deal that preserves Trump’s 25% automotive tariff, according to people familiar with the conversations. That impasse continues.

On Monday, Trump appeared to cut off talks with Tokyo. Japan “won’t take our RICE, and yet they have a massive rice shortage," he posted on Truth Social, despite Japan importing hundreds of thousands of tons of U.S. rice annually under a WTO agreement. Trump added that “we’ll just be sending them a letter"—a reference to his repeated pledges to dictate to trading partners what they would have to pay the U.S.

In a Fox News interview the previous day, Trump had suggested what such a letter to Japan might say: “Dear Mr. Japan, here’s the story. You’re going to pay a 25% tariff on your cars, you know? So we give Japan no cars. They won’t take our cars."

After slapping so-called reciprocal tariffs on dozens of countries on what Trump dubbed “Liberation Day"—then putting them on hold—the White House vowed to strike a spate of trade deals before July 9. The standoff with Japan shows how hard that is turning out to be.

Administration officials attempting to negotiate multiple deals have at times contradicted one another about goals and timelines, and Trump has further muddied the picture with references to sending letters. Adding to the uncertainty is an appeals court hearing set for late July over the legality of the emergency authority Trump used to impose the so-called reciprocal tariffs.

Even the tariff deadline is in question. On Friday, after Treasury Secretary Scott Bessent indicated some countries could get an extension, Trump injected further uncertainty. “We can do whatever we want," he said in a news conference. “We can extend it, we can make it shorter. I’d like to make it shorter." On Tuesday, Trump he’s “not thinking about" extending the deadline.

The chaotic situation has left Japan and other countries bewildered, unsure of what the White House wants or when they have to deliver a deal. Thus far, the administration has cut only a limited trade agreement with the U.K. and struck a tariff truce with China. Hanging over the entire process is Trump’s earlier promise to restore the Liberation Day tariffs on countries that don’t do deals—potentially triggering another round of market chaos.

The chaotic situation has left Japan and other countries bewildered. Cranes at a shipping terminal in Yokohama.

White House spokesman Kush Desai said the administration “continues to work around the clock with our trading partners to renegotiate lopsided trade deals that have left American industries and workers behind," and that the White House is on the brink of securing more deals.

Sen. Kevin Cramer (R., N.D.), a close Trump ally who said he has discussed the negotiations with trade representative Greer, said in an interview that deals might take more time than the administration has let on.

“It’s easy to get the framework together, and that’s where they are, but in terms of the actual details, it takes a long time," Cramer said, adding that he has confidence in the negotiation process. “Maybe they set a little bit of an ambitious expectation."

Early optimism

In April, Peter Navarro, Trump’s senior trade and manufacturing adviser, said the administration could land 90 deals in 90 days. After the U.S. struck the limited agreement with the U.K. in early May, Trump said he believed the deals would start flowing at a rapid pace.

Administration officials looked to Japan to keep the momentum going. Tokyo had signed a trade deal with the U.S. during Trump’s first term. U.S. officials believed Japan had an incentive to reach an agreement: A favorable deal could bolster the minority government of Japanese Prime Minister Shigeru Ishiba.

The U.S. complicated its negotiating position with Japan and other countries by increasing tariffs as talks progressed, such as in June when Trump doubled global steel tariffs with no warning for trading partners. Other so-called national-security tariffs on products such as lumber, semiconductors and critical minerals remain in the planning process, making some nations hesitant to strike deals before they are unveiled. The administration’s bellicose approach also became a political issue in some countries it was negotiating with, encouraging resistance to the U.S. rather than cooperation.

Japanese Economic Revitalization Minister Ryosei Akazawa, right, with Treasury Secretary Scott Bessent, center, and Commerce Secretary Howard Lutnick in Washington on May 1.

“We sometimes forget that other countries have politics, too, and trade has a way of spurring on domestic politics because of the direct and indirect effects it has on particular constituencies," said Michael Froman, U.S. trade representative under former President Barack Obama and current president of the Council on Foreign Relations.

Since Trump paused reciprocal tariffs on April 9, the leader of Japan’s negotiating team, Economic Revitalization Minister Ryosei Akazawa, has visited Washington seven times. His team has been in near constant contact with staffers for Bessent and Greer, who are leading the U.S. talks together with Lutnick.

Trump’s reciprocal tariffs for Japan had been set at 24% before the pause—far above the roughly 1.5% average tariffs that had been in place, according to the Richmond Fed. Besides seeking a reduction to those, Japanese officials have said repeatedly they cannot agree to any deal that doesn’t reduce industry-specific tariffs, particularly after the U.K. received some relief from steel and auto tariffs. In June, after another round of talks, Akazawa said all U.S. levies must be reduced in any deal.

Privately, some Japanese officials worry that agreeing to a deal that doesn’t reduce or eliminate both the reciprocal tariffs and industry-specific duties might be received so poorly in Tokyo that it could topple the Ishiba government, which is facing a high-stakes election to the Japanese parliament’s upper house on July 20. Any deal that reduces Japanese protections for its prized domestic rice industry could also spell electoral trouble for the Ishiba government.

In June, Prime Minister Ishiba flew to Canada for a leadership summit of the Group of Seven industrialized nations hoping to force a compromise, but a meeting between Trump and him yielded no breakthrough.

Japanese Prime Minister Shigeru Ishiba flew to the G7 summit hoping for a breakthrough.

“There are still points where our views remain divided," Ishiba told reporters. “Automobiles are a major national interest…and we will continue to do everything we can to protect such interests."

A senior lawmaker in Japan’s ruling Liberal Democratic Party said that some of Ishiba’s associates are arguing that he should hold firm to his demand for tariff relief in the hope that Trump backs down, perhaps if financial markets grow unsettled as the end of the 90-day tariff pause nears.

A senior Trump administration official said the president’s advisers have discussed the possibility of implementing further tariffs on Japan if a deal can’t be reached. The two sides appear to remain far apart on key issues like the auto tariffs, said people with knowledge of the talks. As of late June, they hadn’t even decided whether any deal would include those levies or focus only on the reciprocal tariffs.

An official from Greer’s office told The Wall Street Journal the administration is prioritizing negotiations with trading partners who have presented more serious offers than Japan has.

Mounting difficulties

Canada and the U.S. have yet to reach a deal after Trump doubled tariffs on the country’s steel industry without warning in June. A U.S. official familiar with a G-7 meeting between Trump and Canadian Prime Minister Mark Carney said each team has more work to do to even come close to a deal, with differences ranging from Canada’s digital-services tax to its tariffs on dairy products.

On Friday, Trump said he cut off negotiations with the Canadian government and that he would notify the nation within a week about the tariffs he would impose. After Canadian officials on Sunday scrapped a plan to implement the digital-services tax, the two countries announced they would restart negotiations.

Trump doubled tariffs on Canada’s steel industry without warning in June. Steel coils at a mill in Hamilton, Canada.

The U.S. and South Korea are redoubling negotiating efforts after a new government took power in Seoul last month. South Korea wants relief from tariffs on autos, steel and aluminum. Its proposed regulations on U.S. e-commerce firms doing business in South Korea have drawn the ire of Greer and American firms such as Google and Coupang, further complicating negotiations.

U.S. negotiators raised the digital trade issue with South Korea’s new trade negotiator, Yeo Han-koo, when he visited Washington in late June, said people with knowledge of the talks, but a deal isn’t imminent.

Elsewhere in Asia, the U.S. is demanding that nations take a hard line against China. The administration is struggling to finalize pacts with Vietnam and Cambodia, despite offers from those nations to reduce tariffs and trade barriers, according to people with knowledge of the talks.

The White House wants Southeast Asian nations in particular to prevent China from shipping goods to the U.S. through their countries, to stop Chinese companies from setting up manufacturing and export operations in their countries, and to set their own tariffs and trade restrictions on Chinese goods, according to people with knowledge of the talks.

Many of those nations are balking at being forced to choose between the U.S. and China, making any deals on those issues unlikely in the short term. One Asian economic official said the U.S. demands would be difficult to meet, given that the export-led economies in the region are so entwined with both the U.S. and China.

Trump speaking at the G7 summit in June. From left: Treasury Secretary Scott Bessent, Secretary of State Marco Rubio, U.S. Ambassador to Canada Pete Hoekstra. and Canadian Prime Minister Mark Carney.

The administration has appeared to make progress with the European Union, but domestic political considerations on the continent threaten to hamper Trump’s goals. After the Journal reported on a draft “agreement on reciprocal trade" setting out possible EU concessions on a range of policy issues, European Commission President Ursula von der Leyen pushed back, saying certain topics legislated by the EU are “absolutely untouchable."

She said the two sides discussed tariff lines, nontariff barriers such as standards and norms, and purchases the EU might make. “But where it is the sovereign decision-making process in the European Union and its member states that is affected, this is too far," she said.

Even some Republicans are growing frustrated with the White House’s negotiating strategy. During a recent Senate Appropriations Committee hearing, Sen. John Kennedy (R., La.) asked, “Are you or are you not pursuing reciprocity?" when Lutnick said he wouldn’t agree to a hypothetical deal with Vietnam that would cancel out all tariffs and trade barriers in both countries.

Kennedy later said: “I was confused more after the hearing than before about their negotiating strategy here."

Write to Gavin Bade at gavin.bade@wsj.com and Brian Schwartz at brian.schwartz@wsj.com