Although it has very few ingredients, this soup is intensely flavorful because the squash is browned before it's simmered. Simmering it in coconut milk instead of stock makes it extra rich and creamy. Don't skimp on the drizzle of olive oil at the end; it's there not only for presentation, but also to balance the flavor.
Add 1 tablespoon of the olive oil to a Dutch oven or large pot and heat over medium-high heat. Add half the squash and 1 teaspoon salt. Cook, stirring occasionally, until the bottom of the pot and some of the squash pieces are browned, 4 to 5 minutes. Transfer the squash to a bowl. Add the remaining 1 tablespoon olive oil and uncooked squash to the pot with 1 teaspoon salt. Cook, stirring occasionally and deglazing the brown bits on the bottom of the pot with a splash of water and a wooden spoon if it looks like it's going to burn, about 4 minutes. Add the rest of the cooked squash back to the pot.
Add the coconut milk and apples to the pot and bring to a boil. Reduce to a simmer and cook until the squash is quite tender, 15 to 20 minutes. Puree with an immersion blender until smooth, or transfer the squash and apple chunks with a slotted spoon to a blender to puree, then return the blended mixture to the pot and stir to combine. Taste and adjust the seasoning as necessary.
Serve the soup topped with apple slices and big drizzles of olive oil.
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