Preheat oven to 350 degrees. Line a large baking sheet with a silpat or aluminum foil.

Toss the cubed bread with 4 Tbsp olive oil and crushed garlic cloves. Empty out onto the lined baking sheet. Bake for 15 minutes until the cubes of bread are crisp on the outside. Set aside.

In a large cast iron skillet, heat 2 Tbsp olive oil over high heat. When hot, add the cored roma tomatoes to the pan. You’ll want to essentially blister or char all sides of the tomatoes. Once the sides are blistered and blackened, reduce heat to low and continue to cook while you prepare the rest of the soup.

In a large soup pot, heat 1 Tbsp olive oil. Add sliced garlic cloves, shallot, and red pepper flakes. Season with salt and pepper, and stir in the oregano. Cook over low heat for approximately 4 to 5 minutes, or until the shallots are translucent. Add canned diced tomatoes and cook 12 to 15 minutes, stirring occasionally. Finally, stir in heavy cream and water.

If you have an immersion blender, add the charred tomatoes to the sauce pot and blend the mixture together until mostly smooth (I like my soup to have a little texture but you can blend until completely smooth if desired). If you don’t have an immersion blender, used a standard blender and blend the soup together in batches (first the soup base in the soup pot, then the charred tomatoes, and combine in the soup pot to finish). Season with salt and pepper to taste.

Serve the tomato soup warm with the garlic croutons.