Analysis by Rob Picheta, CNN
CNN — The relative calm in Ukrainian cities far from the country’s battlefields was shattered by two painfully familiar sounds this week: the ominous ring of the air raid sirens, and the eruptions of Russian attacks.
A wave of missiles, rockets and drones has struck dozens of locations across Ukraine since Monday, according to officials, targeting civilian infrastructure in several major cities, including Kyiv, located hundreds of miles from the front lines in the east and south.
The wide bombardment echoed the early days of Russia’s scattershot initial invasion in February, but also underlined that the conflict in Ukraine, which for months appeared to be descending into a slow and painful grind in the Donbas, has erupted once again as winter nears.
Not for the first time, the war is teetering towards an unpredictable new phase. “This is now the third, fourth, possibly fifth different war that we’ve been observing,” said Keir Giles, a senior consulting fellow at Chatham House’s Russia and Eurasia Programme.
The strikes followed weeks of Ukrainian ground gains and began two days after a huge explosion damaged the Kerch bridge, the only crossing between the annexed Crimean peninsula and Russia. That blast, which was used by the Kremlin as a justification for Monday’s onslaught, bruised the Russian psyche and handed Ukraine a significant strategic boost.
With the cold months nearing and likely bringing a slowdown in ground combat, experts say the next weeks of the war are now expected to be vital, and another potential spike in intensity looms over Ukraine as each side seeks to strike another blow.
“What seemed a distant prospect for anything that could be convincingly described as a Ukraine victory is now very much more plausible,” Giles said. “The response from Russia is likely to escalate further.”
‘Playing for the whistle’
Monday’s attacks, and further strikes throughout the week, were evidence of Russian President Vladimir Putin lashing out after a series of setbacks in the war that have put him under pressure domestically.
And the airborne strikes distract from what has been a dismal stretch for Russia in the ground war.
Oleksii Hromov, a senior Ukrainian military official, said last week that Kyiv’s forces have recaptured some 120 settlements since late September as they advance in the Kharkiv, Donetsk and Kherson regions. On Wednesday, Ukraine said it had liberated more five settlements in its slow but steady push in Kherson.
These counter-offensives have shifted the momentum of the war and disproved a suggestion, built up in the West and in Russia during the summer, that while Ukraine could stoutly defend territory, it lacked the ability to seize ground.

“Russia’s Road to War with Ukraine” author and senior fellow at the International Institute for Strategic Studies Samir Puri told CNN that the Russians are “playing for the whistle” in an effort to prevent a frontline collapse before winter sets in.
“Given how badly this has been handled since February, if they can get to Christmas with the frontline looking roughly as it is, that’s a huge success for the Russians.”
The Kremlin named a new overall commander of Russia’s invasion in response to mounting setbacks. However, given the speed and expense of the Ukrainian counteroffensives, there is little evidence that Gen. Sergey Surovikin can guide his forces back onto the offensive before the end of the year.
Moscow is probably preparing to defend the cities of Starobilsk and Svatove in the Luhansk region, while Ukrainian troops are primarily focused on driving Russian forces east after crossing the Oskil River in late September, according to the Institute for the Study of War (ISW).
Landing a decisive blow in Donbas would send another strong message, and Ukraine will be eager to build on its successes before battlefield temperatures drop and the full effects of rising energy prices are felt throughout Europe.
There are numerous reasons why Ukraine is motivated to complete tasks quickly, according to Giles. “Ukraine and its Western backers will always have to demonstrate their resiliency in the face of the winter energy crisis in Europe and the destruction of energy infrastructure and power in Ukraine itself.”
NATO leaders have vowed to support Ukraine no matter how long the conflict lasts, but several European nations, particularly those that depended heavily on Russian energy, are facing a crippling cost-of-living crisis that, in the absence of indications of Ukrainian military progress, could jeopardize public support.
In the meantime, recent events have demonstrated that locations outside the current theater of ground combat are not immune to attacks. The Kerch bridge bombing’s precise method of execution is still unknown, and Kiev has not taken responsibility. However, the fact that a target so far into Russian-controlled territory could be hit with such accuracy suggested that Ukraine posed a serious threat to important Russian assets.
Russia scrambles for manpower
Russia is struggling on the ground and has failed to achieve supremacy in the air, but Monday’s attacks may have achieved one goal – sending a signal of strength towards the growing list of Putin’s internal critics.
The assault damaged civilian infrastructure in cities all across Ukraine, killing multiple people and knocking out power in pockets of the country. They were “an indication of the nature of the threat from Russia,” Giles said. “For many months now, the Russian objective has been to destroy Ukraine rather than possess it.”
Ukraine’s national electricity company, Ukrenergo, says it has stabilized the power supply to Kyiv and central regions of Ukraine after much of the country’s electricity supply was disrupted by Russian missile attacks on Monday and Tuesday. But Ukrainian Prime Minister has warned that “there is a lot of work to do” to fix damaged equipment, and asked Ukrainians to reduce their energy usage during peak hours.
Experts believe it remains unlikely that Russia’s aerial bombardment will form a recurrent pattern; while estimating the military reserves of either army is a murky endeavor, Western assessments suggest Moscow may not have the capacity to keep it up.
“We know – and Russian commanders on the ground know – that their supplies and munitions are running out,” Jeremy Fleming, a UK’s spy chief, said in a rare speech on Tuesday.
That conclusion was also reached by the ISW, which said in its daily update on the conflict Monday that the strikes “wasted some of Russia’s dwindling precision weapons against civilian targets, as opposed to militarily significant targets.”

“Russia’s use of its limited supply of precision weapons in this role may deprive Putin of options to disrupt ongoing Ukrainian counter-offensives,” the ISW assessed.
Exactly how much weaponry and manpower each side has left in reserve will be crucial to determining how the momentum will shift in the coming weeks. Ukraine said it intercepted 18 cruise missiles on Tuesday and dozens more on Monday, but it is urging its Western allies for more equipment to repel any future attacks.
“The barrage of missile strikes is going to be an occasional feature reserved for shows of extreme outrage, because the Russians don’t have the stocks of precision munitions to maintain that kind of high-tempo missile assault into the future,” Puri said.
Some help for Putin may be on the way, however. An announcement by Belarusian President Alexander Lukashenko that Belarus and Russia will “deploy a joint regional group of troops” raised fears of deepened military cooperation between the close allies and that Belarusian troops could formally join Russia in its invasion. Belarus has been complaining of alleged Ukrainian threats to its security in recent days, which observers say could be a prelude to some level of involvement.
The impact of such an intervention in terms of pure manpower would be limited; Belarus has around 45,000 active duty troops, which would not significantly bolster Russia’s reserves. But it would threaten another assault on Ukraine’s northern flank below the Belarusian border.
“The reopening of a northern front would be another new challenge for Ukraine,” Giles said. It would provide Russia a new route into the Kharkiv oblast (region), which has been recaptured by Ukraine, should Putin prioritize an effort to reclaim that territory, he said.
Any further Belarusian involvement in the war could also have a psychological impact, Puri suggested. “Everyone’s mind in Ukraine and in the West has been oriented towards fighting one army,” he said. Inside Russia, Belarus joining the invasion “would play into Putin’s narrative that this war is about reuniting the lands of ancient Rus states.”
A plea to the West
By flipping the narrative of the conflict over the past two months, Ukrainian President Volodymyr Zelensky has achieved one of his own key objectives: showing Ukraine’s Western allies that their military aid can help Kyiv win the war.
Now Zelensky will hope for more supplies in the short-term as he seeks to drive home those gains. The leader has sought to highlight Ukraine’s success in intercepting Russian missiles, saying more than half of the missiles and drones launched at Ukraine in a second wave of strikes on Tuesday were brought down.
NATO Secretary General Jens Stoltenberg said Tuesday that Ukraine needed “more” systems to better halt missile attacks, ahead of a meeting of NATO defense ministers in Brussels.
“These air defense systems are making a difference because many of the incoming missiles [this week] were actually shot down by the Ukrainian air defense systems provided by NATO Allies,” he said.
“But of course, as long as not all of them are shot down, of course there is a need for more,” Stoltenberg added.
According to Justin Bronk of the London-based Royal United Services Institute (RUSI), Ukrainian interception success rates against Russian cruise missiles have increased significantly since the beginning of the invasion in February. He made this observation to CNN.
According to Bronk, Ukraine “badly needed” contemporary systems like the NASAMS anticipated from the United States and the IRIS-T that arrived this week from Germany.
Ukraine will be keeping an eye on the West’s resolve to maintain its resolve if Russia tightens energy supplies even more than it is already doing.
There are many things Russia can do to make the conflict personal for people throughout Europe, not just in Ukraine, according to Giles, in an effort to put pressure on governments to stop supporting Ukraine.
The airstrikes this week may be a step in that direction. According to Ukraine’s Energy Minister Herman Halushchenko, Russian missiles struck about 30% of Ukraine’s energy infrastructure on Monday and Tuesday. The minister claimed to CNN that Russia had “dramatically targeted” energy infrastructure for the “first time since the start of the war.”
According to experts, the upcoming weeks will therefore be crucial on the battlefield as well as in Europe and other parts of the world. Where Putin goes next, as always, depends on how the rest of the world reacts, according to Giles. “The failure of Western nations to confront and deter it has shaped Russia’s attitude,”
It implies that as winter draws closer, the stakes of the conflict have once again increased. Russia would undoubtedly like to continue, Giles said. However, the Kremlin has also received a clear message as a result of recent Ukrainian victories. Let’s get used to it, Giles said, “because they can do things that surprise us.”