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To underscore the potential pain for Russia, the chairman of the Joint Chiefs of Staff, Gen. Mark A. Milley, spoke with his Russian counterpart two weeks ago and delivered a stark message: Yes, he said, you could invade Ukraine and probably roll over the Ukrainian military, which stands little chance of repelling a far larger, better armed Russian force. But the swift victory would be followed, General Milley told Gen. Valery Gerasimov, by a bloody insurgency, similar to the one that led to the Soviet retreat from Afghanistan more than three decades ago, according to officials familiar with the discussion. General Milley did not detail to General Gerasimov the planning underway in Washington to support an insurgency, a so-called “porcupine strategy” to make invading Ukraine hard for the Russians to swallow. That includes the advance positioning of arms for Ukrainian insurgents, probably including Stinger antiaircraft missiles, that could be used against Russian forces.