Preheat oven to 425 degrees F. Use a spoon to clean out seeds and strings from the pumpkin's center. Slice pumpkin halves into 2 - 3 equal pieces. Brush all over with 2 tablespoons olive oil and sprinkle with sea salt. Arrange skin side down on baking sheet. Roast until squash is fork tender with brown edges, 30 - 35 minutes. When pumpkin is cool enough to handle, scoop flesh from skins, mash pumpkin with a fork and set aside.

Meanwhile, set a large stockpot over medium heat. Add 2 tablespoons olive oil, and when hot, toss in onions. Cook, stirring often, until onions are translucent, 5 - 7 minutes. Add garlic, chili powder, and a pinch sea salt, and sauté 1 minute. Stir in broth, 1 cup water, and mashed pumpkin. Bring mixture to a boil, then turn heat to medium-low, simmer 20 minutes.

Working in batches, puree soup in a blender until very smooth. If needed, add up to 1 cup more water. 

Pour pureed soup back into stockpot and warm soup over medium-low heat. Taste, and add sea salt or chili power as needed.

Meanwhile, set a small skillet over medium heat and add 2 tablespoons olive oil. When oil’s hot, add sage leaves, cook 15 - 20 seconds, flip with tongs, and cook 15 - 20 seconds longer. Set sage on a paper towel-lined plate.

In the same skillet, still over medium heat, add pepitas and a pinch sea salt. Cook just until pepitas pop, 1 - 2 minutes. Set pepitas in a bowl and toss with sea salt and chili powder.

Ladle soup into bowls. Garnish with crumbled fried sage leaves, toasted pepitas, and a drizzle of olive oil. Serve immediately.