Preheat your oven to 400°F (200°C). On a baking sheet, arrange the tomatoes and garlic. Drizzle with olive oil, sprinkle with salt and pepper. Roast for about 1 hour until caramelized.

Heat olive oil in a Dutch oven over medium heat. Add chopped onion and sauté for 3-4 minutes until tender. Stir in oregano and cayenne pepper.

Incorporate roasted tomatoes and garlic, vegetable broth, and basil into the Dutch oven. Simmer for 15-20 minutes.

Remove from heat and blend the soup to desired consistency. Stir in half-and-half cream.

Ladle soup into bowls and garnish with fresh cracked pepper. Serve hot with crusty bread or grilled cheese.