The US mocked Russia for its motley cast of allies in Ukraine. It's not laughing any more.

• Russia's dealmaking with Iran and North Korea has attracted mockery from the West as "desperate."
• But what appeared a motley alliance is cementing the power of all three countries, experts said. 
• It's helped Russia in Ukraine — and North Korea is likely to be doing well out of it. 

In the fall of 2022, President Vladimir Putin was in a bind. Expecting to have already overrun Ukraine, his forces were instead being routed from huge swathes of the country.

"They just didn't have the weapons they needed. They didn't have the soldiers prepared. They didn't have the defensive positions prepared," RAND defense researcher Bruce W. Bennett told Business Insider.

Isolated from much of the world by sanctions, Putin turned to rogue states like Iran and North Korea for munitions.

The US will have watched very closely. But publicly, officials were sanguine, even dismissive.

Secretary of State Anthony Blinken quipped in September that the rag-tag partnerships came off like a "Star Wars bar scene of countries."

"Nothing from Pyongyang will be a game changer in Ukraine," Mark Milley, then-chairman of the Joint Chiefs of Staff, remarked in September last year.

More recently, UK Defence Minister Grant Shapps poked fun at Putin by saying he had humiliatingly gone "cap in hand" to North Korea to support his war machine.

But as Western support wavers, the impact of Pyongyang's ammunition supply — along with bombardments of Iranian Shahed drones — is likely giving Russia a distinct edge in Ukraine, experts said.

And beyond Ukraine, it is having ripple effects on the international order.

Tipping the scales

The three-way axis is "fragile in many ways," Beth Sanner, a former intelligence official under the Trump and Biden administrations, said at a recent Atlantic Council event.

But, she said, it has "a quite serious and very real effect."

As Russia's invasion stalled in mid-2022, Putin had already started the groundwork to procure Shahed drones from Iran.

Russia has fired thousands of them across Ukraine since then.

Given that neither Russia nor North Korea has admitted to arms transfers, there is no way of knowing exactly how significant their contribution is to Russia's wider supply of munitions for the war.

But "the volume of stuff that's been going over is huge. It's significant," Joseph Byrne, an open-source researcher and North Korea specialist at the Royal United Services Institute, told BI.

Since September, South Korea says that it has observed North Korea sending about 6,700 containers to Russia, potentially holding about three million 152mm artillery shells, or half a million 122 mm shells.

Bennett said this is a "major contribution" to Russia's war efforts, even factoring in the possibility that many of the shells — likely drawn from Soviet-era stockpiles — may be duds.

And North Korea's factories are now working round the clock to bring Russia fresh weapons and shells, South Korea said on Wednesday.

Asked if these supplies were a "game changer" for Russia, John Herbst, a former US ambassador to Ukraine, put it bluntly.

They're a "game continuer," he told the Atlantic Council.

Given Ukraine's desperate ammunition shortages, that may be all Putin needs.

Last year, Russia was estimated to be burning through 30,000 shells a day in Ukraine — roughly what the US could produce in a month at the time, Bennett said.

The US has since ramped up production, but "it's going to take us years to get anywhere close to what North Korea has been providing to Russia," he told BI.

Byrne added: "You see Russia's ability to continue to fire artillery, fire rockets on Ukrainian positions just massively increase and sustain over a long period of time, very likely because of this uplift from the North Koreans."

Going rogue

Despite the criticism of his allies, Putin is showing little sign it bothers him.

To work with North Korea, Putin has contravened UN Security Council resolutions he himself signed onto.

For Bennett, Putin's thinking is simple. "If Russia failed to achieve success in Ukraine, meaning it got pushed out of Ukraine, is Putin going to survive physically?" he asked. "The answer is probably no. So Putin's desperate."

Motivated by self-preservation, Putin has little reason to mind the jibes of Ukraine's allies.

"What matters is power," Bennett said.

A boon for North Korea

Much the same can be said for Kim Jong Un, whose regime shows signs of gaining a great deal from the partnership.

The terms of the exchange are unknown, but Byrne outlined several ways North Korea might benefit.

Cold hard cash is one.

Thanks to international sanctions, North Korea is obliged to hold much of its money abroad, Byrne said.

Western intelligence officials recently told The New York Times that Russia had unfrozen millions of dollars of North Korean assets in a possible exchange for ammunition supplies.

Another area of gain is technological: It might be sophisticated technology transfers for electronic warfare systems, air defense systems, and ballistic missiles, Byrne said.

The opportunity to see how its homegrown ballistic missiles perform on the battlefield is also "absolutely invaluable" for Kim, Byrne said.

South Korea has accused its northern neighbor of using Ukraine as a test site for its nuclear-capable missiles.

Meanwhile, Russia has already been seen boosting North Korea on the international stage, like in September when Russia's foreign minister, Sergei Lavrov, suggested that UN sanctions against the country were outdated.

Operating like this "really emboldens North Korea, Iran, and any other autocratic state," said Sanner.

An opportunistic cartel

It's unlikely that ties between Moscow and Pyongyang run deep, since they have little basis in shared ideology, experts said.

In supplying weapons, Kim Jong Un's regime is unlikely to be driven by a dislike of Ukraine, Bennett said.

"But they sure love Russian money and they sure love Russian grain," he said, describing it as "more a cartel kind of relationship."

But as shallow as the ideological kinship might run, there is little doubt Russia's dealmaking with Iran and North Korea has changed the picture, he said. Signs of that are already emerging — in January, Russia and Iran announced their intention to sign a wide-ranging treaty.

"Two years ago, people would've said, 'well, Russia's got some power, but not a big deal. Iran, oh, it's a nuisance, but it's not a big deal. North Korea's a nuisance, we're worried about their nukes, but not a big deal,'" Bennett said

Now, he said, "all three countries look more powerful, more threatening. And so yeah, it's changed the landscape."