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Step 1
Preheat oven to 425°F (220°C).
Step 2
Slice squash vertically down the center, scoop out the seeds, and place the halves cut-side down on a baking sheet lined with parchment paper. Rub 1 tablespoon of olive oil on the outside skin of the squash, and bake in the oven for about 30 minutes (or until almost tender).
Step 3
Allow squash to cool, peel the skin off, and cut squash into 2-inch cubes. Set aside.
Step 4
Next, in a large pot, heat remaining 1 tablespoon of olive oil over medium-high heat. Saute onions until slightly brown, about 3-4 minutes, adding a pinch of salt as they cook. Stir in garlic, ginger and cayenne pepper and cook for 1 more minute.
Step 5
Add 2 cups of the stock, brown sugar (or maple syrup), and squash and bring to a boil. Cover, reduce heat, and simmer for about 10-15 minutes (or until the squash is very tender). Remove from heat.
Step 6
Puree soup with an immersion blender or puree in batches in a regular blender or food processor, adding remaining stock slowly until the soup reaches the desired consistency.
Step 7
Season with salt and pepper to taste and garnish with optional toppings.