The missiles were a shock in this western Ukrainian city spared from much of the war, a place so far from the front lines it does not even have a curfew. When the mayor heard the first strike, he thought it was thunder.
But the target and timing of the cruise missiles were even more surprising. They hit a factory run by an American multinational, best known for making coffee machines, six days after President Trump met President Vladimir V. Putin of Russia in Alaska to discuss ending the war in Ukraine.
“Two hits in one location?” asked Andriy Baloha, the mayor of Mukachevo. “No, they didn’t mess up. They knew exactly where they were hitting.”
A week later, two missiles hit central Kyiv, damaging the offices there of the European Union and the British Council, a cultural organization. Russia typically avoids striking that area, where foreign diplomatic missions are concentrated. Ursula von der Leyen, the president of the European Commission, accused Moscow of intentionally targeting the European Union.
Striking American and European assets, analysts and government officials said, sent a confrontational message: Mr. Putin feels empowered to rebuff pressure to make peace, to wage war as he sees fit, and even to inflict pain on the West in the process.
Mr. Trump has been calling for direct peace talks between Mr. Putin and President Volodymyr Zelensky of Ukraine, while European countries are discussing what security guarantees to provide Ukraine after the war to prevent another Russian invasion. The Kremlin has dismissed negotiations as premature and Western security guarantees as unacceptable.
“Russia is now striking at everyone in the world who seeks peace,” Mr. Zelensky said.
Russia launched hundreds of drones and missiles on Thursday at Kyiv, the capital, killing at least 25 people in the deadliest civilian strikes since Mr. Trump met with Mr. Putin. None of the fatalities were at the diplomatic buildings.
“Putin is very cautious, and what he does has a certain goal,” said Oleksandr Merezhko, chairman of the foreign affairs committee in the Ukrainian Parliament. Striking Western targets, he added, is “a clear signal from him that he feels confident, and that he is waging the war not only against Ukraine but also against the West.”
After the attack in Mukachevo, Mr. Trump said that he was “not happy” with it and that he had expressed his displeasure to Mr. Putin. After the attack in Kyiv, Mr. Trump was also “not happy,” said Karoline Leavitt, the White House press secretary. But that has been the extent of the American response; the president’s threats of additional sanctions against Russia have remained only threats.
“The escalation reflects Moscow’s calculated assessment that it can impose costs on Western support without triggering direct military retaliation,” said Franz-Stefan Gady, a military analyst based in Vienna.
“Russia is effectively testing the boundaries of Western deterrence while pursuing a broader coercive strategy aimed at weakening allied resolve and forcing Ukraine toward unfavorable negotiating positions,” he added.
Among other measures, Europe is debating sending peacekeeping troops to Ukraine.
The message from Moscow is “don’t you dare send your troops here, because Ukraine is somewhere we can strike anywhere we like,” said Volodymyr Dubovyk, the director of the Center for International Studies at Odesa I.I. Mechnikov National University.
A new minerals deal signed in the spring between the United States and Ukraine aims to attract American investors to Ukraine — which American leaders have suggested could be its own kind of security guarantee. But it’s unclear how American companies would be protected from future Russian attacks.
Just over half of American companies in Ukraine have been damaged in Russian strikes, including a McDonald’s, a building used by Boeing and a Philip Morris factory.
The Flex Ltd. factory that was struck on Aug. 21 in Mukachevo, a city of 86,000 people, is the largest employer in the region.
Company officials and Ukrainian officials said that nothing weapons-related was made in the plant, though some technology used in consumer products can be converted to military use. A Flex spokeswoman declined to talk to The New York Times for this article, saying the company was focused “on our teammates, the site assessment and recovery.”
The Russian Ministry of Defense said its strikes in Mukachevo targeted “enterprises of the Ukrainian military-industrial complex.” Foreign Minister Sergey V. Lavrov of Russia initially claimed to NBC News that he had “never heard about” the attack on the Flex plant but also that Russia “does not target civilian facilities.”
The Flex plant has floor space equal to about 10 football fields. It employed 5,400 people before the invasion, and about 3,000 when it was struck. The company is based in Austin, Texas, and Singapore and is publicly traded on the Nasdaq stock exchange. It began operating in far-western Ukraine about 25 years ago because of tax incentives, Mr. Baloha, the mayor, said.
It contracts with other companies to build consumer products, he added: lamps for Philips, phones for Nokia, cartridges for Xerox. Its main contract now, Mr. Baloha said, is making coffee machines for Nespresso.
“I have three at home,” he added.
Prime Minister Yulia Svyrydenko of Ukraine quipped on social media that Russia had decided to “liberate” Ukraine from coffee machines.
Mukachevo lies in an area known as Transcarpathia, a small slice of Ukraine west of the Carpathian Mountains. Hundreds of miles from the front lines, the region has been largely spared from Russian strikes, possibly because it borders the NATO countries of Hungary, Poland, Romania and Slovakia. Drones have rarely been spotted.
The signs of Flex’s importance here are everywhere. Among the roadside signs written in the Cyrillic alphabet, those for the plant spell out “Flextronics,” the company’s former name, in Latin letters. Last year, Flex paid more than $8 million in taxes, making it the largest taxpayer in Transcarpathia, Mr. Baloha said.
On Aug. 21, the air raid alarm went off at 4:30 a.m. Most of the city ignored it, but the 600 workers on the Flex night shift headed for the factory shelter.
The first missile hit seven minutes later, shattering the sense of security the region had. The blast threw a nearby convenience store manager’s bed up into the air and woke a soldier with the call sign of Rabbit who was recuperating from losing his right leg in combat.
“Police officers were even standing nearby, and no one reacted — no one understood what it was,” said Anton Slava, 25, a truck driver who was at a gas station.
“The car jolted — you could feel the blast wave,” he recalled.
As Mr. Slava drove to work, crossing a bridge near the Flex plant, he saw the telltale rising red dots of interceptor missiles trying to knock out a second missile. They failed, and it hit the plant.
Yevheniia Shvanda, 31, has worked at Flex for seven years. Although she is on maternity leave, she immediately heard from colleagues who fled to the shelter. Twenty-seven were wounded, none seriously. The company is planning to reopen.
“Flex was the first factory that welcomed us, gave us jobs, gave us opportunities,” Ms. Shvanda said. “It’s really devastating that this happened. That factory was my whole life. It felt like a big family to us.”
Kim Barker is a Times reporter writing in-depth stories about the war in Ukraine.
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