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Step 1
Preheat the oven to 350 degrees F (175 degrees C).
Step 2
Arrange tomatoes cut-side up on 1 or 2 large 4-sided baking pans. Place unpeeled garlic on top of tomatoes. Drizzle with olive oil and sprinkle with coarse salt.
Step 3
Roast in the preheated oven for 1 hour. Remove from the oven and let cool in the pan.
Step 4
Meanwhile, heat butter in a large stockpot over medium-low heat. Cook onion, sugar, and oregano in the hot butter until onion is softened, 5 to 7 minutes. Peel roasted garlic and add to the pot. Add roasted tomatoes and their juices. Pour in vegetable stock. Cover and let soup simmer for 20 minutes.
Step 5
Puree soup using an electric blender working in batches, using extreme caution with hot liquids; vent the lid a bit and cover with a old towel. Force puree through a mesh strainer into another pot, discarding solids.
Step 6
Stir in heavy cream and season soup with salt and pepper.