Five crucial questions as Russia-Ukraine war enters winter

As winter sets in across Ukraine, Russia’s aerial assaults on the country show no sign of letting up.

Even as Kremlin forces pound Ukraine’s cities and key infrastructure, Kyiv’s military has proven resilient, pushing Russian troops out of occupied territory in eastern and southern Ukraine. 

Further shoring up Ukraine’s military is a steady flow of U.S. and European military and humanitarian support, including another $400 million lethal aid package the U.S. government announced Wednesday filled with critically needed air defense ammunition.  

The Western weapons have helped keep Russia on its back foot and blunted its missile barrage, but with Moscow looking to weaponize winter by knocking out Ukraine’s energy system, the world is closely watching how the season will affect the fight.  

Here are five crucial questions as the Russia-Ukraine war enters winter.  

How much will winter play a role in the fight? 

As fighting drags into its 10th month, the conflict is expected to taper incrementally as winter settles over Ukraine and cold conditions worsen. 

Though Ukraine has been successful in its counteroffensive launched in September to liberate occupied lands, Russia currently remains in control of roughly 20 percent of Ukraine’s territory. That includes much of the eastern part of Ukraine, such as the Donetsk and Luhansk provinces and Crimea. 

Under Secretary of Defense for Policy Colin Kahl said last week that “sloppy weather in Ukraine” has already slightly slowed the battle, with muddy conditions making it hard for either side to execute a major offensive.

“I think that that challenge is going to get worse in the coming weeks, so we’ll have to see whether the fighting slows down as a consequence of that,” he told reporters.  

In preparation for the harsh winter, the U.S. has sought to provide the country with cold weather gear, including tens of thousands of parkas, fleece hats, boots and gloves, in addition to generators and tents, according to the Pentagon. 

How much will Ukrainians suffer in the cold?

Ukraine is fielding a relentless Russian aerial bombardment on major population centers and energy infrastructure across the country.

Moscow’s barrage of missile and drone strikes, which have picked up since October, also employs Iranian-provided kamikaze drones to target major cities and cause maximum damage. 

On Nov. 14 alone, Russia launched an estimated 60 to 100 missiles at numerous Ukrainian cities. 

Among the attacks was one on Ukraine’s power grid last week that caused “colossal” damage, with no thermal or hydroelectric power plant in the country now intact, according to the head of Ukrenergo, the government-owned electricity transmission system operator.  

The results have been catastrophic, with Ukraine’s energy ministry on Wednesday noting that the Kremlin attacks have caused the “vast majority of electricity consumers” to lose power. 

Though Ukraine has scheduled blackouts to conserve energy, its civilians are expected to suffer heavily during winter, with 2 million to 3 million individuals likely to be displaced in the coming months as the weather grows colder, according to Hans Henri P. Kluge, the World Health Organization’s regional director for Europe.

And Gen. Mark Milley, the chairman of the Joint Chiefs of Staff, said last week that with the onset of winter, “families will be without power, and more importantly, without heat,” which is expected to cause “incalculable human suffering.” 

“Basic human survival and subsistence is going to be severely impacted, and human suffering for the Ukrainian population is going to increase,” he told reporters. “These strikes will undoubtedly hinder Ukraine’s ability to care for the sick and the elderly. Their hospitals will be partially operational. The elderly are going to be exposed to the elements.”  

Can Russia take territory in the east?  

Russia has been pounding the eastern cities of Avdiivka and Bakhmut for weeks, creating conditions that Ukrainian President Volodymyr Zelensky has described as “just hell.” 

And it’s only getting worse. The shelling in the eastern Donetsk region has escalated this week, and war observers say Russia could send more troops and weapons to the east after retreating from Kherson in the south.  

“The enemy does not stop shelling the positions of our troops and settlements near the contact line,” the General Staff of the Ukrainian Armed Forces said on Tuesday. 

“They continue firing at the critical infrastructure and civilian housing. … In the Bakhmut and Avdiivka directions the enemy is focusing its efforts on conducting offensive actions.” 

Ukraine, however, has managed to hold on so far.  

Last month, reports spread among war watchers that Wagner paramilitary forces — which are leading Russia’s efforts in Donetsk — had been given a deadline to take Bakhmut by the end of October, with Putin desperate for a win to offset mounting losses elsewhere.  

If Ukraine loses Bakhmut, it could allow Russia to advance to other key cities in Donetsk, which is among the regions annexed by Moscow in late September.  

Russia has plenty of reinforcements to draw on, between more than 20,000 troops who were previously in Kherson, to the nearly 200,000 reservists reportedly being mobilized to join the war in the months ahead.  

Yet even Yevgeny Prigozhin, the Russian oligarch and war hawk who founded the Wagner Group, has recognized that Ukraine’s military is making progress slow.   

“Our units are constantly meeting with the most fierce enemy resistance, and I note that the enemy is well prepared, motivated, and works confidently and harmoniously,” Prigozhin said in a statement released last month. “This does not prevent our fighters from moving forward, but I cannot comment on how long it will take.” 

Will Russia’s mobilization start to make a difference? 

It’s been more than two months since Putin took the dramatic step of mobilizing military reservists, potentially adding some 300,000 troops to his war effort in Ukraine.  

The move had an immediate impact in Russia, bringing the war closer to home for thousands of families whose sons and fathers were called up to join the “special military operation.”  

But it was expected to take months before the reservists could be trained, equipped and sent off to battle. Even then, wide skepticism remains about what impact, if any, the reservists might have against well-trained and determined Ukrainian military units.  

The Institute for the Study of War has reported that — despite Russian mobilized personnel continuing to protest and desert — the first groups of the new forces have been trained and are being deployed in the annexed Zaporizhzhia, Luhansk and Donetsk regions in the east.  

“Russian forces will likely continue to use mobilized and redeployed servicemen to reignite offensive operations in Donetsk Oblast and maintain defensive positions in Luhansk Oblast,” the institute wrote earlier this month.  

The Kremlin is also reportedly preparing a “second wave” of mobilization to begin in December and January, meant to bolster Russia’s forces next spring and summer.  

Whether those larger numbers can overcome the morale and logistics challenges that have plagued Moscow’s forces thus far remains to be seen. 

Could the two sides talk? 

As fighting rages in Ukraine, the United State and other Western backers are grappling with how hard to push Kyiv to move toward peace negotiations with Moscow. 

Earlier this month, Milley said that there may be a window for negotiations to end the war, as Russian forces are “really hurting bad” after nine months of conflict, during which they have failed at “every single” objective. 

“You want to negotiate at a time when you’re at your strength and your opponent is at weakness,” Milley told reporters last week. “It’s possible, maybe, that there’ll be a political solution. All I’m saying is there’s a possibility for it. That’s all I’m saying.”  

But Milley also highlighted the realities of the battle ahead with winter so close. 

The probability of a Ukrainian military victory, in which the Ukrainians push all Russian forces from the country, including Crimea, “is not high,” he predicted.  

Those comments came one week after Milley appeared to push for negotiations at an event in New York, telling attendees that both sides should accept that military victory is impossible and a negotiated end to the war necessary.

“When there’s an opportunity to negotiate, when peace can be achieved, seize it,” Milley said. 

The White House, however, has stressed that Washington is not trying to coerce Kyiv to hold talks with Moscow or give up any territory. 

Zelensky “gets to determine if and when he’s ready for negotiations and what those negotiations look like,” national security spokesman John Kirby told reporters last week.  

“Nobody from the United States is pushing, prodding or nudging him to the table,” he added. 

Also driving speculation about possible upcoming talks is Zelensky earlier this month dropping demands that Putin be out of power before any negotiations are agreed to.