2 teaspoons Extra Virgin Olive Oil (more Or Less As Needed)
1 cup Vegetable Stock
¼ cups Heavy Cream
Croutons, To Garnish
Preheat oven to 300ºF. Line a baking sheet with heavy duty foil; set aside.
Drain tomatoes, saving the juices for preparing the soup (you should about 1 1/2 cups reserved). Slice the tomatoes in half and place cut-side up on the prepared baking sheet. Sprinkle with salt, pepper and brown sugar. Drizzle with olive oil and roast in the preheated oven for one hour. Remove tray from oven and let cool for 10 minutes.
Transfer cooled tomatoes to the blender bowl attachment on your Cuisinart stand mixer. Add the vegetable stock and blend until smooth. Pour soup into a 2-quart pot and heat until warmed, but not boiling. Stir in the cream and cook for one more minute. Serve garnished with croutons.