Kim Jong-Un and Putin Meet in Russia: Ukraine War Live Updates

A Ukrainian attack targeting the headquarters of Russia’s Black Sea Fleet in Crimea damaged two ships and triggered a large blaze at a sprawling naval shipyard that plays a critical role in the Russian war effort, according to Russian and Ukrainian officials.

The pre-dawn attack on Wednesday appeared to be the largest on the Russian naval headquarters in the occupied port city of Sevastopol since Moscow launched its full-scale invasion of Ukraine nearly 19 months ago and underscored Ukraine’s growing capacity to hit targets deep into Russian-held territory.

The Russian Ministry of Defense said in a statement that Ukraine had fired 10 cruise missiles at the facility at the same time as it targeted a Russian warship on the Black Sea with three maritime drones. Air defense systems shot down seven cruise missiles, and the patrol ship Vasily Bykov destroyed the unmanned drones, the ministry said.

Moscow’s rare acknowledgment of a successful Ukrainian attack in Crimea came only after local residents posted images of explosions and raging fires at the Sevmorzavod shipyard on social media. Mikhail Razvozhaev, the Russian-backed governor of Crimea, later shared a photo that appeared to show the port side of a large landing ship on fire, though the full extent the damage was not clear.

Mr. Razvozhaev said that at least 24 people were injured at the shipyard. The initial explosions, and sounds of air defenses, were first reported at about 2 a.m. local time.

It was unclear what weapons Ukraine deployed in the assault, but the commander of the Ukrainian Air Force, Lt. Gen. Mykola Oleshchuk, suggested that a long-range airstrike was involved.

“While the occupiers are still recovering from the nighttime bombardment in Sevastopol, I would like to thank the pilots of the Ukrainian Air Force for their excellent combat work,” he wrote in a statement. “To be continued …”

Mykhailo Podolyak, a senior presidential adviser, hinted that the attack was carried out using new weapons. He said in a statement that the only way to secure trade routes and grain shipments through the Black Sea was to build up Ukraine’s armed forces capacity, “including by expanding the range of weapons.”

“We can already see the results of this” in Sevastopol, he wrote.

He did not elaborate on what weapons were used. This summer, Ukraine acquired long-range weapons from the British and French, and Kyiv has also been developing its own domestically produced long-range cruise missiles.

The attack damaged an improved Kilo-class attack submarine, the Rostov-on-Don, and a Ropucha-class landing ship, the Minsk, according to Russian military bloggers and the Russian news outlet Baza, which did not cite sources.

The reports could not be independently confirmed, but Russian officials said the attacks had damaged two ships that were in dry dock. A satellite image taken by Planet Labs on Tuesday shows a Ropucha-class ship and an apparent submarine in the dry dock. Imagery from Planet Labs after the attack showed the ship and what appeared to be burn damage to the dry dock, though the resolution made the submarine harder to make out.

The attack on the Russian naval fleet comes only days after Ukraine said its forces had retaken several oil and gas drilling platforms on the Black Sea, which have played a role in Russia’s ability to project power off Ukraine’s coast since Moscow seized them in 2015.

Russian forces used the platforms, known as the Boyko Towers, as forward deployment bases, installing radar installations, long-range missile systems and a host of other equipment. Dmytro Pletenchuk, a spokesman for the Ukrainian Navy, said driving Russian forces off the platforms “allows us to keep them devoid of pertinent information, rendering them unable to react promptly or plan anything within our waters.”

Around the same time as the Russian port was coming under attack, the Ukrainian military said that it shot down 32 of 44 Iranian-made attack drones that were mainly targeting port and grain infrastructure in the Odesa region.

Oleh Kiper, the head of the Odesa military administration, said that the ports on the Danube River on the border with Romania were targeted once again and that seven civilians had been injured.

“We’re dealing with the aftermath,” he said in a statement. “Firefighters are working on containing the fire.”

Christiaan Triebert contributed reporting.