Preheat the oven to 425°F. On a parchment paper–lined baking sheet, place the cauliflower pieces in a single layer. Brush with 1 tablespoon of olive oil, and then sprinkle with 1⁄8 teaspoon of pepper. Bake for 25 minutes. Remove from the oven and set aside.

In a high-speed blender, combine the tomatoes, almond milk, tomato paste, roasted peppers, coconut sugar, the remaining tablespoon of olive oil, sea salt, and remaining 1⁄8 teaspoon of pepper. Blend until smooth. Transfer the soup to a large saucepan. Set the heat to medium-high and warm the soup for about 5 minutes.

Ladle the soup into bowls and top each with the roasted cauliflower.