Preheat oven to 425F. Line a rimmed baking pan with parchment paper.
Add the sliced butternut squash, halved tomatoes, and basil to the prepared pan. Drizzle one tablespoon olive oil on top. Season with the dried herbs, salt, and black pepper. Toss to combine.
Slice the top half of the garlic head off to expose the garlic cloves. Place on the pan and drizzle with the remaining olive oil.
Roast for 20-30 minutes, until the butternut squash is fork-tender.
Transfer the mixture to a food processor or blender. Add the vegetable stock and pulse until smooth and creamy.
If needed, heat on the stove top until desired temperature. Add heavy cream to taste.
For the crispy pancetta topping, add a little olive oil to a skillet over medium high heat.
Add the chopped pancetta and sage leaves. Saute until crispy and golden brown.
Serve on top of the plated soup with a small slice of brie and freshly cracked black pepper.
Enjoy with Klarbrunn Pomelo Grapefruit Sparkling Water for a complimentary drink!