Vladimir Putin’s journey to Pyongyang to meet fellow dictator Kim Jong-un is emblematic of the Russian leader’s isolation. Just 10 years ago, he was attending meetings of the G8 (now the G7) and rubbing shoulders with the leaders of the world’s richest nations. Now he has to go cap in hand to the pariah state of North Korea to seek both support for his war in Ukraine and the weapons to pursue it.

Russia’s military cooperation with Iran, North Korea and China has expanded into the sharing of sensitive technologies that could threaten the U.S. and its allies long after the Ukraine war ends, according to U.S. defense and intelligence officials.

The speed and depth of the expanding security ties involving the U.S. adversaries has at times surprised American intelligence analysts. Russia and the other nations have set aside historic frictions to collectively counter what they regard as a U.S.-dominated global system, they said.

It must be somebody pretty important in your life to warrant a personal airport pickup at 3 a.m. But that’s the honor North Korean “Supreme Leader” Kim Jong Un paid to Vladimir Putin on Wednesday morning, greeting the Russian President on a red carpet-laid runway in the wee hours and then riding with him through Pyongyang streets festooned with roses and murals of his stout, balding guest, whom Kim had earlier hailed as an “invincible comrade-in-arms.”