Preheat oven to 400°F. Toss cubed squash with 1 Tbsp olive oil and sugar and spread out in a single layer on a sheet pan. Roast for 20–30 minutes or until tender and beginning to brown, gently stirring halfway through roasting. Set aside.

In a medium pot, heat 2 Tbsp olive oil over medium high heat. Add onion and garlic and sauté 4–6 minutes or until softened. Add apples and thyme and sauté 5 minutes more. Add broth and 1 cup water and bring to a boil. Reduce to a simmer and cook 10–15 minutes or until apples are tender. Stir in roasted squash to combine.

Puree soup in batches in a food processor or blender until very smooth. If soup is too thick, add additional water until desired consistency is reached. Return to pan and season with sugar and salt.

Divide between bowls and garnish with thinly sliced apple, pepper and pumpkin seeds.