In a large pot, heat 2 tablespoons of olive oil and 1 tablespoon of butter over medium heat. Add the diced onion, chopped celery (with leaves), and minced garlic. Sauté for about 5 minutes until the vegetables soften and become fragrant.

Stir in the whole peeled tomatoes and light brown sugar with the sautéed vegetables. Pour in the chicken bone broth and bring the mixture to a gentle boil. Reduce the heat to low, add the fresh thyme, and let the soup simmer partially covered for 15–20 minutes so the flavors meld together.

Remove the sprig of thyme, then use an immersion blender to blend the soup until it is smooth and creamy. If you don’t have an immersion blender, you can carefully transfer the soup in batches to a regular blender, then return it to the pot.

Return the blended soup to the pot over low heat. Stir in the heavy cream until fully combined, and season with salt and black pepper to taste. I like to add a good amount of freshly ground black pepper at this stage to really enhance the flavors.

Bring the creamy tomato soup back to a gentle simmer. Add the ravioli directly to the soup and cook until the ravioli float to the top; this should take just a few minutes.

Ladle the hot soup and ravioli into bowls. Garnish with fresh basil leaves, an extra drizzle of cream if you’d like, and a final sprinkle of black pepper before serving.