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Preheat oven to 375°F. Line a baking sheet with foil.
Heat 2 tablespoons oil in a large saucepan over medium heat until shimmering. Add onion, carrots and parsnip and cook until the onions are translucent, about 6 minutes. Add squash, apple, curry powder, 2 cloves garlic and ginger and cook, stirring, until fragrant, 1 to 2 minutes. Add broth, tomatoes and lentils and stir to combine. Bring to a boil. Reduce heat to maintain a low simmer, cover and cook until the squash and lentils are tender, about 20 minutes.
Meanwhile, brush one side of each naan with the remaining 1 tablespoon oil. Sprinkle with the remaining 1 clove garlic and place on the prepared baking sheet. Bake until warmed, 5 to 6 minutes. Remove from oven and sprinkle with cilantro.
Gently mash some of the soup with a potato masher to achieve desired consistency. (Alternatively, transfer half the soup to a blender and puree. Use caution when blending hot liquids.) Garnish the soup with cilantro and serve with the naan.