Ukraine’s 10 Most Daring Military Operations So Far

Ukraine isn’t a military superpower. It doesn’t have endless stockpiles or manpower, and it can’t rely on overwhelming force to win battles. Instead, it depends on coordination, adaptability, and a military that has learned to seize every opportunity as it appears.

To protect its civilians and keep its cities safe, Ukraine has relied on air defense. Alongside systems like Patriot and IRIS-T, it has begun deploying tools like SkySentinel—a crowdfunded, AI-powered turret designed to intercept drones and fill critical gaps in coverage.

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But while systems like SkySentinel protect Ukraine’s cities from incoming strikes, the daring operations behind Russian lines prevent many of those attacks from happening at all by disrupting Russia’s ability to launch, resupply, or coordinate.

Here are ten of the boldest so far.

1. Snake Island: Ukraine’s first punch

On day one of Russia’s full-scale invasion, Russia stormed Snake Island—a bald, sea-lashed slab of rock floating 120 kilometers off Odesa’s coast. Strategically, it’s just a dot on the map. But in naval warfare, elevation and line-of-sight matter more than size. Whoever holds Snake Island can see what moves through the northwest Black Sea and hit it. Russia knew that. So did Ukraine.

The Russians took it fast. A small group of Ukrainian border guards held the post, outgunned and isolated. One of them, Roman Hrybov, gave the world a perfect war slogan when he radioed back: “Russian warship, go fuck yourself.” They were captured, not killed, and later exchanged in a POW swap. Meanwhile, Russia dug in, accumulating missiles, radar, artillery, and supply drops. It was a miniature fortress on a rock.

Ukraine answered with Neptune missiles and drone strikes, then sent in the special forces. SBU, HUR, and Navy commandos flew in low on helicopters, dodged radar, landed into a minefield, and fought their way across the rock. Russian troops tried to blow the whole thing — mines, soldiers, the works. They failed. On June 30, 2022, Russia fled. 

2. Hostomel Airport and the defense of Kyiv

On the first morning of the full-scale invasion, Russia tried to end the war in a single move. The plan was to land troops at Hostomel Airport, secure it fast, and turn it into a launchpad for thousands more. Within hours, Russian forces would be inside Kyiv. It was supposed to be quick, overwhelming, and over.

But Ukraine’s National Guard units and paratroopers from the 80th Brigade met the landing force head-on, destroying the runway before it could be used and turning the airport into a battlefield. The fight raged for nearly two days. Helicopters were shot down. Airborne units were wiped out. Russia’s lightning strike slowed to a crawl, then stopped.

Russia’s capture of Hostomel Airport was meant to fast-track the fall of Kyiv, a quick decapitation strike to install a new regime within days. However, Ukraine’s rapid response halted the plan in its tracks. What was supposed to be a three-day war turned into a long, grinding fight that no one expected Ukraine to survive, let alone win battles in. What happened in Hostomel changed the entire course of the war.

3. The sinking of the Moskva

Ukraine doesn’t have a traditional navy. What it does have is ingenuity and the will to improvise. Ukrainian forces pulled off in April 2022 what no one had done before: they sank a Russian missile cruiser in active combat. The target was the Moskva, the flagship of Russia’s Black Sea Fleet. 

The weapon? A pair of domestically developed Neptune missiles, retrofitted and launched from a hidden battery near the coast. To make it work, Ukrainian forces sent Bayraktar drones ahead to draw the Moskva’s attention and its air defenses. While the ship was busy swatting at decoys, the real threat came skimming in low over the water. Two hits later, the pride of Russia’s Black Sea Fleet was on fire and eventually sank.

The Moskva represented Russia’s control over the Black Sea and helped coordinate strikes and operations in the southern theater, including those on Snake Island. When the Moskva sank, Russia lost its eyes in the Black Sea. Its radar was gone, its coordination fell apart, and Snake Island was left exposed. That’s when Ukraine moved in with drones, artillery, and eventually, boots on the rock. Snake Island was cleared by the end of June.

The sinking of the Moskva marked a turning point. Ukraine had proven it could hit Russian assets far beyond the front lines without a single warship. Since then, it’s leaned into that strategy, building out a fleet of naval drones to strike ports, bridges, and ships across the Black Sea. This has forced Russia to be more cautious in its naval deployments and reduced the likelihood of amphibious operations. It’s not a traditional navy, but it’s working.

4. The Kherson counteroffensive

When Ukraine launched its counteroffensive in Kherson, no one expected it to work. Russian troops were dug in across the Dnipro River, heavily armed and backed by artillery. The city had been under occupation for eight months. Moscow had already declared it part of Russia. Most analysts assumed it would take years to liberate.

Instead, it took just over two months. Ukrainian forces began pushing south in early fall, using steady pressure, artillery strikes, and HIMARS to isolate Russian units and blow up key supply routes. Bit by bit, Russian positions became unsustainable. Their command was fractured. Their troops were exhausted. And on November 11, 2022, they withdrew from the city by crossing the Dnipro River through the Khahovka dam, which they shortly blew up after.

Kherson became the first and only regional capital that Russia managed to capture, and Ukraine took it back. The footage of civilians waving flags and hugging soldiers flooded the news.

What didn’t make the headlines was what could’ve happened next. Ukrainian forces were reportedly in a position to encircle and capture as many as 30,000 Russian troops retreating across the Dnipro. But that opportunity was cut short after quiet pressure from Washington, according to multiple unofficial accounts. Their goal was to avoid triggering Russian escalation by letting tens of thousands of enemy troops walk free.

5. Kharkiv-Izyum counteroffensive

In September 2022, Ukraine launched a surprise counteroffensive in the Kharkiv region, catching Russian forces off guard with a clever feint involving deceptive troop movements. Russia took the bait. Within days, Ukrainian forces swept through key towns like Balakliia, Kupiansk, and Izyum, reclaiming over 12,000 square kilometers of territory. 

The success of this operation was due to meticulous planning, effective use of intelligence, and the element of surprise. Ukrainian forces employed a combination of mechanized infantry, artillery, and special operations units to exploit weaknesses in Russian defenses and force them into a chaotic retreat. The counteroffensive boosted Ukrainian morale and demonstrated to international allies the effectiveness of their support.

This operation marked a significant shift in the war's momentum, forcing Russia to reevaluate its strategies and redeploy forces from other fronts. It also highlighted Ukraine's growing proficiency in coordinating complex military operations across multiple domains.

6. Crimean Bridge attack

On June 3rd, 2025, the Crimean Bridge took another hit, this time from underwater. In a months-long operation, SBU divers planted 1,100 kilograms of explosives on the underwater supports of Russia’s prized logistics artery. When they blew, they left the bridge in critical condition. No civilians were harmed. Just the structure, which can no longer be considered safe to travel on.

The bridge isn’t just symbolic. It’s Russia’s main logistics artery into southern Ukraine – the only pipeline for troops, fuel, and ammunition from the south. Cutting it means slowing down Russian operations across the entire southern front, a vital step for the Ukrainian Armed Forces to liberate Crimea.

It was the third major strike. The first came in October 2022, when a truck packed with explosives detonated mid-crossing, igniting a fuel train and collapsing large sections of the roadway. Later reports pointed to naval drones joining the attack from below, turning it into a coordinated operation. In 2023, Ukraine hit it a second time.

The bridge was a symbol of Russia’s colonial aspirations, built by Putin to lock in the 2014 attempted annexation, and declare Crimea forever Russian. But each time it gets hit, it says the opposite.

7. Helicopter missions into Azovstal

In March 2022, Russian forces encircled Mariupol, pushing Ukrainian defenders into the Azovstal steel plant that became a massive fortress and last stand for Ukrainian fighters. Over the following weeks, Ukrainian pilots executed a series of perilous helicopter missions to deliver supplies and evacuate the wounded. 

These operations involved flying at extremely low altitudes to avoid detection, facing intense Russian fire. Despite the risks, they successfully evacuated 64 wounded soldiers and delivered 30 tons of cargo. However, the missions came at a cost, with at least three helicopters lost due to Russian anti-aircraft fire. 

The missions were not only logistical feats but also significant morale boosters for the besieged defenders. The presence of reinforcements and the delivery of essential supplies provided a lifeline to those trapped inside Azovstal. The bravery of the pilots and crews involved in these missions has been widely recognized, turning many into overnight heroes.

Ultimately, on May 16, 2022, the defenders of Azovstal were ordered to surrender to preserve lives. Many were taken into Russian captivity, with many remaining unaccounted for. The helicopter missions to Azovstal were carried out by pilots who volunteered, fully aware of the risks of flying into a city under siege with no guarantee of return. 

8. Downing of a Russian A-50U

The A-50 is one of Russia’s most valuable assets in the sky — a flying radar and command center used to track targets, coordinate air operations, and guide missile strikes. The upgraded A-50U version comes with enhanced surveillance systems and was designed to operate far from danger, well behind layers of Russian air defenses. But in January 2024, Ukraine took one down.

The aircraft was flying over the Sea of Azov when it walked into a trap. Ukrainian and British sources say it was hit using a hybrid setup — an old Soviet S-200 missile system paired with a modern American Patriot. The result was catastrophic for Russia. The A-50U was destroyed, marking one of the most embarrassing losses for the Russian Air Force at the time. A second aircraft was reportedly damaged just days later.

This plane played a critical role in coordinating Russian glide bombs and cruise missile strikes in Ukraine. Its destruction forced Russia to pull back its long-range aviation from forward positions, reducing the effectiveness of its targeting and response times. Ukrainian officials noted a measurable drop in guided bomb attacks in the days that followed, giving Ukraine some valuable breathing room.

9. Kursk operation

Ukraine launched a surprise cross-border assault into Russia’s Kursk region in August 2024—the first time since World War II that foreign troops had advanced this deep into Russian territory. Ukrainian units struck fast, capturing villages, taking prisoners, and holding ground for several months.

The goal was to force Russia’s hand and delegate its reserves and other units to protect its rear instead of launching offensives elsewhere in Ukraine. The operation also showed that Russia’s border defenses were vulnerable and that Ukrainian forces could carry out ground raids beyond the front line. It challenged Moscow’s claims of internal security and exposed gaps in its ability to protect key border regions like Kursk.

The raid was a PR disaster for Moscow. Footage of Ukrainian fighters operating openly inside Russian territory made headlines, and the capture of Russian soldiers, including some of the newly arrived North Korean recruits, was an added humiliation. At its peak, Ukraine claimed control over more than 100 settlements and 1,350 square kilometers of Russian territory. Those prisoners would later be traded back in exchanges to recover dozens of Ukrainian POWs. Meanwhile, Russia scrambled to retake the area, launching airstrikes that flattened its border towns and diverting forces away from other key fronts like Kupiansk and Avdiivka. For Ukraine, Kursk was a tactical and psychological win.

10. Operation Spiderweb

On June 1, 2025, Ukraine pulled off one of the most complex drone strikes ever attempted. Operation Spiderweb hit four Russian airbases across multiple time zones — all in a single night. A swarm of 117 drones, smuggled into Russia and hidden in sheds near the targets, was activated remotely and tore through some of the most valuable aircraft in Russia’s arsenal. By the time the sun came up, at least 41 planes were destroyed or damaged, including Tu-95, Tu-160, and Tu-22M3 bombers, and A-50 radar aircraft. Estimated damage: $7 billion. The scale of the hit was so large, Zelenskyy reportedly oversaw it himself.

What made it different wasn’t just the targets but the method. These drones didn’t fly in from Ukraine. They were already inside Russia, hidden in custom-built shipping containers and towed by unsuspecting truck drivers to sites near the airbases. No air raid sirens, no scrambling jets, no warning. They slipped past radar and detonated on the tarmac before anyone knew they were there. 

The bombers and A-50s taken out in the operation were the same platforms used to coordinate and carry out missile attacks on Ukrainian cities. Disabling them meant fewer glide bombs, slower response times, and gaps in Russia’s ability to manage air operations. And Ukraine did it all without a traditional air force, using drones launched from inside Russian territory. Now, for the foreseeable future, a big chunk of the planes Russia uses to bomb Ukrainian cities will be out of action.