• Preheat oven to 400°F (200°C). Line a large sheet pan with parchment paper for easy cleanup.

Prepare vegetables:

• You can leave cherry tomatoes whole.
• Chop Roma and heirloom tomatoes into large chunks.
• Slice the red pepper and onion into wedges.
• Slice the top off the whole head of garlic to expose the cloves and add a little olive oil to the top and wrap in parchment paper.

Roast

• Spread all vegetables onto the prepared sheet pan. Drizzle with 2–3 tablespoons of olive oil, sprinkle with paprika, garlic powder, oregano, salt, and black pepper. Toss lightly to coat. Place the garlic head cut-side down.
• Roast for 30–35 minutes, until tomatoes are blistered, onions are caramelized, and garlic cloves are soft and golden. This step develops the soup’s natural sweetness and depth of flavor.

Blend

• If using a blender or food processor, add vegetables to blender with chicken broth and pesto. Blend until smooth. Add heavy cream and blend again.
• If using an immersion blender, add vegetables to the bowl with broth and pesto. Blend and then mix in heavy cream.

Serve

• Ladle into bowls, garnish with fresh basil, a sprinkle of parmesan cheese, or a swirl of extra pesto. Pair with crusty bread or a grilled cheese sandwich for the ultimate comfort meal.