Roasted Tomato Soup with Grilled Cheese

From the garden

• 3 lb ripe tomatoes, halved through the equator
• 1 medium yellow onion, peeled and quartered
• 4 cloves garlic, unpeeled
• ¼ cup fresh basil leaves

From the pantry

• 3 tbsp olive oil
• 2 cups vegetable stock
• ½ cup heavy cream
• 8 slices sturdy bread
• 8 oz cheddar cheese, sliced
• 3 tbsp butter, softened
• sugar — a pinch, only if the tomatoes taste sharp
• salt — to taste
• black pepper

1. Heat the oven to 425°F. Spread the tomato halves cut-side up on a rimmed sheet pan with the onion quarters and unpeeled garlic cloves. Drizzle with the olive oil, season with salt and pepper, and roast 35–40 minutes until the edges char and the juices concentrate.
2. Squeeze the roasted garlic out of its skins into a soup pot and add the tomatoes, onion, all the pan juices, and the stock. Bring to a simmer for 5 minutes so everything melds.
3. Add the basil and blend the soup until completely smooth — an immersion blender right in the pot is easiest. Stir in the cream, taste, and adjust with salt, pepper, and a pinch of sugar if the tomatoes were sharp. Keep warm over low heat.
4. Butter one side of each bread slice. Build sandwiches with the cheddar inside and buttered sides out, then cook in a skillet over medium heat, 3–4 minutes per side, pressing gently, until the bread is deep golden and the cheese is fully melted.
5. Cut the sandwiches on the diagonal and serve alongside big bowls of hot soup for dunking.