Preheat oven to 375° and line a rimmed baking sheet with parchment. Rub a good amount of olive oil over cut side of squash; place cut side down on baking sheet and place in oven. Cook squash until fork tender – about 50-65 minutes. Let the squash cool until it’s ready to handle. Scoop squash out into a bowl and set aside.
In a large soup pot, heat olive oil and coconut oil over medium heat. Add sliced leeks and oregano, and sauté until leeks are soft; add garlic and cook for 30 seconds. Add the fennel and ginger, and cook for about 5 minutes – until fennel is soft and ginger is fragrant. Add the squash, bay leaf, water, salt, and pepper – stir.
Whisk the coconut milk, lemon juice, cayenne, salt, and pepper.
Turn the heat up and bring soup to a simmer, cook for roughly 30 minutes, stirring every so often. Remove from heat and stir in 1 cup spicy coconut cream.
In batches, puree soup in a blender, or food processor, until smooth. Transfer soup back to the pot and bring to a low simmer, stir in lemon juice and taste for seasoning.
Serve soup with a dollop of leftover spicy coconut cream, poppy seeds, and chopped fennel fronds.
Note: just about any variety of squash works well here, just be mindful that if it’s smaller than a kabocha squash you will need to adjust the amount of liquid, seasoning, etc.
Adapted from Dolly and Oatmeal.