KHARKIV, UKRAINE — Kupyansk was one of the first Ukrainian cities to fall to the Russians during the opening days of the war. It is only 25 miles from the border, and many of its 26,000 residents speak Russian. One of its major political parties supported the Russian state.

On February 27, 2022, when Russian columns rolled through, the mayor, Hennadiy Matsegora, was a member of that party. He surrendered immediately. In a video broadcast, he told his constituents that Russia would not intervene in their daily lives so long as they avoided “provocations,” by which he meant things as simple as speaking the Ukrainian language or resisting Russian authorities when they interfered with the curriculum in local schools.

The occupation lasted six months. On September 6, 2022, a daring Ukrainian counteroffensive pushed along the back roads around Kupyansk, encircling Russian forces. By the end of the month, the city was back in Ukrainian hands, where it has remained for the last three years. There has been no end to the suffering, however. The city’s strategic importance—there is a crucial railway junction in Kupyansk—has meant that Russians forces have shelled it on a near daily basis. Most of Kupyansk has been destroyed, and 90 percent of its inhabitants have fled, many to nearby Kharkiv.

And now, to add insult to injury, the city—and the region in which it lies—might find itself back in Russian hands. It is near the top of Vladimir Putin’s wish list in a potential land-swap deal, whereby Ukraine would cede territory to Moscow in exchange for a freeze in hostilities.

In Washington, that deal has drawn a mixed response. President Trump said in August that “some land-swapping between Russia and Ukraine” might end the war, perhaps even “to the good of Ukraine.”

But more recently, he has struck a different tone. “Ukraine. . . is in a position to fight and WIN,” Trump posted to Truth Social last Tuesday. “The original Borders from where this War started is very much an option.”

The outcome of this debate carries existential consequences for cities across eastern Ukraine. Where the border lines are drawn will determine whether their citizens must become Russian.

The people of Kupyansk don’t need to imagine what this would be like: They already know what Russian occupation would mean. During the first six months of the war, their mayor’s promises of Russian noninterference proved empty. Instead, what followed was a brutal battle for hearts and minds—waged against the city’s children.

“When the Russians gained control, we noticed right away that their first priority was replacing our education with the Russian program,” Sergey Shadanovsky, now the head of the Kupyansk Education Department, told me.

The outcome of this debate carries existential consequences for cities across eastern Ukraine. Where the border lines are drawn will determine whether their citizens must become Russian.

“They destroyed Ukrainian books, diplomas, certificates—any symbol that showed that Ukrainian education was real and different from the Russian curriculum,” he explained. Russian occupying authorities declared that children will “become educated citizens of their country, Russia.” Students speaking the Ukrainian language in school received beatings.

Meanwhile, they were told to hate Ukraine. The newly introduced Russian textbooks portrayed Ukraine’s current government as a “neo-Nazi state”—a baseless claim promoted by the Kremlin to justify its invasion.

“The newly introduced Russian textbooks portrayed Ukraine’s current government as a ‘neo-Nazi state,’ ” writes Aidan G. Stretch. (© 2022 Human Rights Watch/CC BY-NC-ND 3.0 US)

“ ‘Denazification’ in the official Russian usage just means the destruction of the Ukrainian state and nation,” Timothy Snyder, a historian of Eastern Europe, wrote shortly after the war began.

The Kremlin is still pushing this line. At his recent Alaska summit with President Trump, Putin insisted that the goals of the military operation in Ukraine have not changed: Ukraine must be “denazified.”

In Kupyansk, Russian authorities gave school officials an ultimatum: Begin teaching the Russian curriculum or do not return to the school.

Like the mayor, some teachers were willing to collaborate with the Russian regime, often because of the salary rather than the ideology. At one school in Kupyansk, 81 out of 82 teachers worked with the Russian occupation, by far the highest proportion in the Kharkiv region.

Natalia Patrova, the principal at Lyceum No. 4, a secondary school in the center of the city, refused to cooperate, seeing the Russians as the enemy. “We were never going to leave our community to the enemy, and we wanted to make sure all of our students and families knew that,” she told me.

“Russian occupiers imprisoned and beat teachers, even subjecting some of them to electroshock torture for refusing to cooperate,” writes Aidan G. Stretch. (via author)

The question was: How to get this message out?

At the time, Patrova was living 10 kilometers outside Kupyansk. She tried to reach her school by car, but Russian military checkpoints blocked her. Communicating over the phone was risky too: Local officials collaborated with the Russians, which meant widespread surveillance. Still, Patrova risked sending simple messages on Telegram channels to her school’s families: “Your teachers are not leaving. We will stay, and we will continue to teach you.”

These short messages were incredibly dangerous. Elsewhere in the region, Russian occupiers imprisoned and beat teachers, even subjecting some of them to electroshock torture for refusing to cooperate. Shadanovsky, who was then the deputy head of the Education Department, never witnessed these tactics in Kupyansk. But he did see other forms of coercion.

“When we refused their demands, soldiers brought us to the school and forced us to sign papers announcing our resignations,” Shadanovsky said. “We didn’t see another paycheck or receive humanitarian aid for months.”

Meanwhile, “the Russians offered teachers 10,000 Russian rubles [about $125] and access to humanitarian aid if they collaborated,” Shadanovsky told me. “That may not sound like much, but for people who. . . had families to feed, it was a hard offer to turn down.”

Like the mayor, some teachers were willing to collaborate with the Russian regime, often because of the salary rather than the ideology.

Before the start of the new school year, in September 2022, educators who agreed to the Russian demands worked with authorities to transform Lyceum No. 4 into a Russian school—where students studied the virtues of Russia’s “special military operation” and learned why Ukraine should not be considered an independent nation.

Patrova and Shadanovsky, however, spent the summer helping their students get Ukrainian qualifications. “We wanted to make sure our students had the credentials to eventually attend university in Ukraine,” Patrova said.

This meant finding a way for students to take the National Multisubject Test (NMT), the college entrance exam. In Kupyansk, options were limited. The fighting had destroyed the city’s communications infrastructure. So Patrova, Shadanovsky, and other former faculty at Lyceum No. 4 began driving students through Russian checkpoints to Slovyanoserbsk—a village almost 200 kilometers to the southeast—where they could use public computers to register for the entrance exam.

The exam itself took place in Kharkiv, 120 kilometers to the west, via a road with Russian checkpoints that allowed students—but not adults—to cross.

And so the dissident teachers explained to their pupils how to travel, alone, to get their qualifications.

A few days into the new school year, on September 9, 2022, images began to circulate on social media of Ukrainian forces raising flags near buildings that looked like the Kupyansk city hall. A day later, the Kharkiv Region Administration confirmed the rumors: A daring counteroffensive had driven Russian forces from the city.

Days later, Patrova returned to her school, for the first time since the war began, to find appliances ripped out of the walls and classrooms empty, save for a few boxes of Russian textbooks. She began cleaning, tossing out the invaders’ propaganda and scavenging for any remaining Ukrainian textbooks.

“It was an indescribable time,” Patrova told me. “We were now back undoing the Russian education, just as they had done to us before.”

Reckoning with the full effects of the occupation, though, would prove more complicated than swapping out textbooks.

With Ukrainian authorities back in charge, the head of the Kupyansk Education Department was quickly arrested, tried, and given a five-year sentence for collaborating with the Russian occupiers. Shadanovsky, who was his deputy at the time, took his place. “The other qualified candidate had already fled to Russia in the face of his own pending collaboration charges,” Shadanovsky told me.

Many collaborators stayed behind, but most were never charged. “Rounding up everyone tainted by collaboration would be impossible,” one Ukrainian investigator explained to The Wall Street Journal. “There are just too many.” Educators, nurses, and other municipal employees had worked openly with the Russian soldiers in Kupyansk; some had even dated them.

In Kupyansk, reckoning with the full effects of the Russian occupation would prove more complicated than swapping out textbooks.

At Lyceum No. 4, most of the teachers who had worked with the Russians remained in their jobs. Across the region, Ukrainian courts found only 35 educators guilty of collaboration activities.

Some residents complained that collaborators were getting off too easily. Others took their grievances much further: On June 8, a gunman killed Hennadiy Matsegora, the collaborationist mayor, outside his home in Belgorod, Russia, where he fled following Kupyansk’s liberation.

Patrova’s own feelings were mixed. “I do not blame people who worked with the Russians because they had to feed their families,” Patrova told me. “But for those who openly welcomed the occupation or thwarted our efforts to teach our Ukrainian programs, it is a different story. We do not speak to them.”

After Ukrainian troops took back Kupyansk, the city was shelled almost daily. By late 2024, Russian forces were attacking sometimes up to 19 times a day. Kupyansk became uninhabitable. In October 2024, the Kharkiv regional governor ordered the evacuation of all civilians from the city.

“I was tasked with overseeing the evacuation of our schools,” said Shadanovsky, whose house was destroyed. “But I did not want to leave. I now wait every day until I can return.”

Like most former residents of Kupyansk, he now lives in Kharkiv, which experiences daily attacks from Russian missiles, drones, and glide bombs.

“After Ukrainian troops took back Kupyansk, the city was shelled almost daily,” writes Aidan G. Stretch. (via author)

Since the evacuation order, battlefield reports from Kupyansk have been increasingly grim. The city lacks water, gas, and electricity as Russian drones patrol the skies. Few buildings remain intact.

“We prefer to imagine our houses how they used to be. We do not ask for any news of what has happened to them,” Natalia Laptev, a Ukrainian literature teacher at Lyceum No. 4, told me.

Three out of Kupyansk’s 10 schools remain standing. Lyceum No. 4 is one of them, though it will need extensive repairs. It’s too soon to say when the people of Kupyansk may return to restore their schools—if ever. The fact is: If Putin gets his way, a ceasefire deal will render their hometown Russian.

But in the meantime, Patrova is determined to get her students back in the classroom. Distance learning—during two years of Covid and three and a half years of war—has done them irreparable harm. In Kharkiv, seven underground schools have opened to resume in-person instruction, though they will not have enough space for all of the relocated children. One day, Patrova plans to return to Kupyansk.

“I have already reopened my school once. I will do this again. These are my kids, and this is my community,” she told me.

“No matter what happens,” she said, “I will give my students a Ukrainian education.”