Preheat oven to 425°F. Line a large baking sheet with parchment. Peel squash, halve, scoop seeds, and cut into 1-inch cubes. Toss with 1 tablespoon olive oil, ½ teaspoon salt, and ¼ teaspoon pepper. Spread in a single layer on baking sheet.
Chop onion into large chunks and peel garlic. Place on baking sheet with squash, drizzle with remaining 1 tablespoon oil, and toss to coat.
Roast for 25-30 minutes, tossing the squash halfway at 15 minutes, until tender and caramelized. Remove onion and garlic if they finish earlier.
While squash roasts, warm a large pot over medium heat. Add cumin, cinnamon, nutmeg, and cayenne; toast for 60-90 seconds until fragrant. Remove from heat.
Transfer roasted squash, onion, and garlic to the pot. Add broth and bring to a gentle simmer. Cook for 5 minutes, then add 1 teaspoon salt and ¼ teaspoon pepper.
Remove from heat and blend with an immersion blender until completely smooth. If using a countertop blender, work in batches and hold the lid firmly.
Return to low heat, stir in cream, and warm through for 2-3 minutes. Do not boil. Adjust seasoning to taste.
Ladle into bowls and garnish with a swirl of cream, toasted pumpkin seeds, fresh thyme, and a pinch of smoked paprika. Serve hot.