Preheat your oven to 400°F (200°C).

Wash, core, and halve the ripe tomatoes. Quarter the yellow onion and peel the garlic cloves.

Spread the halved tomatoes, onion quarters, and peeled garlic cloves on a large baking sheet.

Drizzle the vegetables with olive oil and season with oregano, thyme, red pepper flakes, salt, and black pepper. Toss to coat evenly.

Roast the vegetables in the preheated oven for 45-60 minutes, until softened and caramelized.

Remove the baking sheet from the oven and let the vegetables cool for 10-15 minutes.

Transfer the cooled roasted vegetables to a blender and add the vegetable broth. Blend until smooth.

Pour the blended soup into a large pot and heat over medium until it simmers, about 5 minutes.

Let the soup simmer for 15-20 minutes, stirring occasionally. Stir in the heavy cream if using.

Taste the soup and adjust seasoning with salt and pepper as needed.

Serve the soup in bowls, garnished with fresh basil leaves and a drizzle of olive oil.