In a 4- to 5-quart saucepan or Dutch oven, heat the olive oil over medium-low heat. When hot, add the leeks, garlic, celery, ginger, and shallots and a pinch of kosher salt. Stir well, cover, reduce the heat to low, and cook, stirring occasionally, until the aromatics are softened, 8 to 10 minutes. Stir in 1 tsp. kosher salt and the paprika.
Add the butternut squash, broth, and wine, stir well, and bring to a simmer over medium heat. Cook, uncovered, stirring occasionally, until the vegetables are very tender and the soup is full-flavored, 7 to 20 minutes.
Take the pan off the heat and let the soup cool for 5 minutes. Working in batches, puree the soup in a blender (fill the jar no more than half full and vent the lid, topping it with a folded kitchen towel to prevent hot splashes). Wipe the pan clean and put the soup back into the pan.
Add the cream and 1/2 tsp. of the vinegar. Season the soup with salt and pepper. Taste the soup and adjust the seasonings with more salt, pepper, or vinegar as needed.
Ladle into 8 soup bowls and garnish each serving with a 1/2 tsp. drizzle of the truffle oil.
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