Roast the tomatoes and garlic: Preheat oven to 425°F (220°C). Place halved Roma tomatoes cut-side up on a parchment-lined baking sheet. Place the garlic head cut-side down wrapped loosely in foil. Drizzle tomatoes with 2 tablespoons olive oil, salt, and pepper. Roast for 25 to 30 minutes until blistered with charred caramelized edges.

Sauté aromatics: In a large Dutch oven or soup pot, heat remaining 1 tablespoon olive oil over medium heat. Add diced onion and carrots, sautéing for 5 to 6 minutes until softened and translucent.

Simmer lentils: Squeeze the soft roasted garlic cloves out of their skins into the pot. Add rinsed red lentils, smoked paprika, and 4 cups of broth. Bring to a boil, then reduce heat to low, cover, and simmer for 15 minutes until red lentils are completely tender and meltingly soft.

Add roasted tomatoes & puree: Scrape the roasted tomatoes and all their pan juices into the pot. Add fresh basil leaves. Use an immersion hand blender directly in the pot to puree the soup until velvety, smooth, and creamy.

Finish with cream: Stir in the heavy cream (or coconut cream). Simmer gently for 2 minutes to meld flavors. Season with additional sea salt and black pepper to taste.

Make dippers & serve: Toast sourdough bread with sharp white cheddar in a buttered skillet until golden-brown and gooey. Cut into slender finger dippers. Ladle steaming hot soup into bowls, swirl with cream, garnish with fresh basil, and serve with crispy dippers!