Roasted Tomato Soup with Grilled Cheese (Printable)

Velvety roasted tomato soup paired with crispy grilled cheese croutons—a comforting, easy dish perfect for cozy evenings.

# Ingredient List:

→ Roasted Tomato Soup

01 - 1.5 lbs ripe tomatoes, halved
02 - 1 medium onion, quartered
03 - 4 garlic cloves, peeled
04 - 2 tablespoons olive oil
05 - 1 teaspoon salt
06 - 0.5 teaspoon black pepper
07 - 1 teaspoon dried thyme or basil
08 - 2 cups vegetable broth
09 - 1 tablespoon tomato paste
10 - 1 teaspoon sugar
11 - 0.5 cup heavy cream or whole milk

→ Grilled Cheese Croutons

12 - 4 slices sandwich bread
13 - 4 ounces sharp cheddar cheese, sliced or shredded
14 - 2 tablespoons unsalted butter, softened

# How-To Steps:

01 - Set oven temperature to 400°F
02 - Arrange tomatoes with cut side up, onion quarters, and garlic cloves on a baking sheet. Drizzle with olive oil and sprinkle with salt, pepper, and thyme or basil
03 - Place in preheated oven for 25 to 30 minutes until tomatoes are soft and caramelized
04 - Transfer roasted vegetables and their juices to a large pot. Add vegetable broth, tomato paste, and sugar. Bring to a simmer over medium heat for 10 minutes, stirring occasionally
05 - Using an immersion blender or carefully in batches with a countertop blender, blend soup until smooth. Stir in cream or milk if desired. Adjust seasoning as needed and keep warm over low heat
06 - Butter one side of each bread slice. Place cheese between two slices with buttered sides facing outward
07 - Heat a skillet over medium heat and cook sandwiches until golden brown and cheese is melted, approximately 2 to 3 minutes per side
08 - Allow sandwiches to cool slightly, then cut into 1-inch cubes
09 - Pour hot soup into bowls and top with grilled cheese croutons

# Expert Advice:

01 -
  • The roasting concentrates the tomato flavor into something almost candy-like, with none of that tinny taste from canned versions.
  • Grilled cheese croutons are basically an excuse to eat tiny sandwiches with your soup, and no one complains about that.
  • You can make the soup ahead and reheat it without losing any magic, which saved me more than once on busy weeknights.
  • It feels fancy enough for guests but easy enough that you will not stress over timing or technique.
02 -
  • Do not skip roasting the tomatoes. I tried this once with raw tomatoes and it tasted flat and watery, nothing like the deep, jammy version you get from the oven.
  • If you blend hot soup in a countertop blender, leave the lid slightly cracked and cover it with a towel. I learned this the hard way when the pressure built up and soup exploded all over my ceiling.
  • Cut the grilled cheese croutons after they cool for a minute or two, otherwise the cheese oozes out and you lose all that gooey center.
03 -
  • Use a rimmed baking sheet for roasting so the tomato juices do not run off and burn in the oven. Those juices are pure flavor and you want every drop in the soup.
  • If your soup tastes too acidic even after adding sugar, stir in a tiny pinch of baking soda. It neutralizes the acidity without changing the flavor, which I discovered by accident one night when I was out of sugar.
  • Press down gently on the grilled cheese sandwiches with a spatula while they cook. It helps them brown evenly and keeps the cheese from sliding out the sides.
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