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Heat the olive oil over medium low heat in a large pot or Dutch oven. Add the red pepper flakes, garlic, and smoked paprika. Cook, stirring constantly until fragrant, about 1 minute.
Turn the heat to medium high, add the butternut squash, roasted red peppers, tomato paste, and salt. Cook, stirring constantly for another 1-2 minutes.
Add the stock, stir until well combined, cover, and bring to a boil. Reduce to a simmer and cook, covered, until the squash is tender, about 20-25 minutes.
Add the coconut milk or cream and red wine vinegar. Using an immersion blender, blend until very smooth and creamy. Alternatively, working in batches, ladle the soup into a blender. Blend on high until smooth, then return to the pot.
Taste and add additional salt or vinegar if desired.