Prep and Roast Tomatoes:

1. Preheat the oven to 400°F and line a baking sheet with parchment paper.
2. Cut the tomatoes into halves or quarters and place them on the baking sheet.
3. Add garlic cloves, drizzle with 1 tablespoon olive oil, and season with oregano, salt, and pepper.
4. Roast for 40-45 minutes until soft and caramelized.

2. Build the Soup Base:

1. In a large pot, heat 2 tablespoons olive oil over medium heat.
2. Sauté chopped onion for 3-4 minutes until softened.
3. Stir in smoked paprika and tomato paste; cook for 2-3 minutes.

3. Add and Simmer:

1. Add the roasted tomatoes, garlic, and vegetable broth to the pot.
2. Toss in fresh basil leaves and bring the mixture to a boil.
3. Reduce heat and simmer for 8-10 minutes.

4. Blend the Soup:

1. Use an immersion blender to puree the soup until smooth. Alternatively, blend in batches using a countertop blender.
2. Stir in Parmesan cheese and brown sugar for added richness.
3. Adjust salt and pepper to taste.

5. Serve and Garnish:

1. Ladle the soup into bowls and top with Parmesan cheese, cracked black pepper, and fresh basil.
2. Serve hot with your favorite bread or croutons for dipping.