Preheat the Oven to 390°F (200°C).
Prepare the Vegetables by peeling and chopping the butternut squash or halving it for roasting.
Season the Vegetables with black pepper, cumin, paprika, thyme, rosemary, and chili flakes. Drizzle with olive oil and toss to coat evenly. If halving the squash, drizzle olive oil on the exposed flesh. Cover with aluminum foil.
Roast for about 1 1/2 hours or until vegetables are golden and soft. Remove foil for the last 10 minutes to caramelize.
Scoop out squash flesh (if halved) and transfer all vegetables to a blender. Add vegetable broth and ginger, blend until smooth and creamy.
Pour the blended mixture into a large pot on medium heat. Stir in coconut milk and warm for 2 minutes.
Adjust seasonings to taste. Garnish with fresh cilantro, a drizzle of coconut milk, and a pinch of chili flakes or chili oil if desired.