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Ukrainian forces pressing an offensive in the south have zeroed in on Kherson, a provincial capital that has been under Russian control since the early days of the crisis.
The possible fall of the city would deal another humiliation to Moscow after a string of battlefield defeats and other setbacks, further cornering Russian President Vladimir Putin and setting the stage for a potential escalation of the nearly eight-month-old crisis.
A look at the military and political importance of Kherson:
Kherson, which had a pre-crisis population of 280,000, is the only regional capital to be captured by Russian forces. The city and surrounding areas fell into Moscow's hands in the opening days of the conflict as Russian troops quickly pushed their attack north from Crimea — the region illegally annexed by the Kremlin in 2014.
Its loss was a major blow to Ukraine because of its location on the Dnieper River, near the mouth of the Black Sea, and its role as a major industrial center. Ukrainian resistance fighters have challenged Russian troops for control of the city ever since, with acts of sabotage and assassinations of Moscow-appointed officials.
Kherson also sits at a point where Ukraine can cut off fresh water from the Dnieper to Crimea. Kyiv blocked those vital supplies after the Crimean Peninsula's annexation, and Putin mentioned the need to restore them as one reason behind his decision.
During the summer, Ukrainian troops launched relentless attacks to reclaim parts of the province, also called Kherson and one of four regions that Russia illegally annexed after sham referendums last month.
Ukraine has used US-supplied HIMARS rocket launchers to repeatedly hit a key bridge on the Dnieper in Kherson and a large dam upstream also used as a crossing point. The strikes have forced Russia to rely on pontoons and ferries, also targeted by Ukraine.
This disrupts supply links to Kherson and the group of Russian forces on the west bank of the Dnieper and makes them vulnerable to encirclement. The shortages were exacerbated after an Oct. 8 truck bomb blew up part of the strategic Kerch Bridge linking Russia's mainland to Crimea, which has served as a major supply hub for the Russian forces in the south.
Putin blamed the Kerch Bridge attack on Ukraine's military intelligence and responded by ordering a bombardment of energy infrastructure across Ukraine.
He also declared martial law in Kherson and the three other annexed regions in a bid to cement Moscow's grip.
But as Ukrainian forces stubbornly pressed its offensive to the southwest alongside the Dnieper, Russian troops have found it increasingly difficult to stem their advance.
General Sergei Surovikin, the newly appointed Russian commander in Ukraine, appeared to set the stage for a possible withdrawal from Kherson, acknowledging the situation in the region was "quite difficult" for Moscow and noting that the combat situation there was still evolving.
Russian authorities, who initially dismissed talk of evacuating the city, sharply changed course this week, warning that Kherson could come under massive Ukrainian shelling and encouraging residents to leave — but only to Russian-held areas.
Officials said 15,000 of an expected 60,000 had been relocated by Thursday. Officials of the Moscow-appointed regional administration also pulled back, along with other civil servants.
Moscow has warned that Ukraine might try to attack the dam at the Kakhovka hydroelectric power plant about 50 kilometres (30 miles) upstream and flood broad areas, including the city of Kherson. Ukraine denies that and, in turn, accused Russia of planning to blow it up to cause catastrophic flooding before its retreat.
Ukrainian President Volodymyr Zelenskyy alleged the dam already was mined by Russia and urged world leaders to make clear to the Kremlin that blowing it up would "mean exactly the same as the use of weapons of mass destruction."
A retreat from Kherson and other areas on the Dnieper's west bank would shatter Russian hopes to press an offensive west to Mykolaiv and Odesa to cut off Ukraine's access to the Black Sea. Such a move would deal a devastating blow to its economy. It would also allow Moscow to build a land corridor to the separatist Transnistria region of Moldova, home to a major Russian military base.
"The loss of Kherson will turn all those southern dreams by the Kremlin into dust," said Ukrainian military analyst Oleh Zhdanov. "Kherson is a key to the entire southern region, which would allow Ukraine to target key supply routes for the Russian forces. Russians will try to retain control of it using all means."
For Ukraine, capturing Kherson would set the stage for reclaiming the Russia-held part of the Zaporizhzhia region and other areas in the south, and eventually pushing back into Crimea.
"Ukraine just needs to wait until Kherson falls into its hands like a ripe apple, because the situation with supplies for the Russian group of forces keeps exacerbating by the day," Zhdanov said.
Ukraine hopes to quickly double the number of US-supplied HIMARS rocket launchers that could strike targets 80 kilometers (50 miles) away with a deadly precision, he said.
Reclaiming control of Kherson would also mean Kyiv could again cut off water to Crimea.
"After the de-occupation of Kherson, the Russians will again have problems with fresh water in Crimea," Zhdanov added.
He said Putin could up the ante if faced with losing Kherson.
"The Russians would be ready to wipe Kherson off the face of the Earth rather than give it to Ukraine," Zhdanov said.
Destroying the dam to cause massive flooding in the mostly flat area would be one way for Moscow to do that.
"The Russians want to show that a Ukrainian counteroffensive will face a tough response by the Kremlin that declared the region as part of Russia, and it's scary to even think what that response could be," Zhdanov added.
Volodymyr Fesenko, head of the Kyiv-based Penta Center independent think tank, noted that capturing all the Kherson region and other southern areas would be a prize for Russia and their loss would have painful consequences for Putin at home and abroad.
"If the Russians leave Kherson, the Kremlin will face another wave of fierce criticism of the military command and the authorities in general from ultra-patriotic circles," Fesenko said, adding that the fall of the city would further demoralize the armed forces and possibly fuel opposition to the mobilization effort.
He also said China and India, which are carefully watching Russia's action in Ukraine, will see the fall of Kherson as a sign of Kremlin weakness.
"Putin will face reputational losses not only inside the country, but also in the eyes of China, and that could be particularly dangerous for the Kremlin," Fesenko said.
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