Preheat your oven to 400°F (200°C) and line a large rimmed baking sheet with parchment paper. Place halved Roma tomatoes, cut-side up, along with quartered shallots. Place the garlic head cut-side up and drizzle all vegetables generously with 3 tbsp olive oil, dried oregano, salt, and pepper.

Roast for 35 to 40 minutes until tomatoes are tender, caramelized, and blistered around the edges, and garlic cloves are golden brown and buttery soft.

Transfer roasted tomatoes and shallots (along with all pan juices) into a 5-quart Dutch oven. Squeeze the soft roasted garlic cloves out of their papery skins directly into the pot.

Add 2 cups vegetable broth and fresh basil leaves. Bring to a gentle simmer over medium heat for 5 minutes.

Using an immersion hand blender, blend the soup directly in the pot until completely smooth and velvety. (Alternatively, blend carefully in batches in a high-speed blender).

Stir in the heavy whipping cream and crushed red pepper flakes. Simmer gently on low for 3 more minutes. Taste and adjust seasoning with additional sea salt and black pepper as desired.

Spread softened butter onto the outside surfaces of the sourdough slices. Pile freshly shredded sharp cheddar and Gruyère between the bread slices.

Griddle in a nonstick skillet over medium-low heat for 3 to 4 minutes per side until golden, crispy, and the cheese is fully melted and stretchy. Slice into dipper sticks or diagonal triangles and serve alongside steaming soup bowls!