Roasted Tomato Soup with Grilled Cheese Croutons

My daughter used to dip everything into soup, no matter what was on the table. One rainy afternoon, she dunked her entire grilled cheese into her bowl and looked up like she'd discovered fire. That moment stuck with me, and I started cutting grilled cheese into cubes so everyone could have their own little dippers. Now it's the only way we serve tomato soup in this house.

I made this for a small dinner party once, and my friend who claims she hates soup had three bowls. She kept fishing out the grilled cheese cubes and said they were like edible spoons. I watched her scrape the bottom of her bowl with one last crouton, and I knew I'd never serve tomato soup plain again.

Ingredients

• Ripe tomatoes: Use the ripest you can find; their natural sugars caramelize beautifully in the oven and create a deeper, richer base than any canned version.
• Onion and garlic: Roasting them whole mellows their sharpness and adds a gentle sweetness that balances the acidity of the tomatoes.
• Olive oil: A good drizzle helps everything caramelize without burning and carries the flavors of the herbs into every bite.
• Vegetable broth: Choose a low sodium version so you can control the salt level, especially after the tomatoes reduce.
• Tomato paste: Just a spoonful intensifies the tomato flavor without making the soup heavy or overly thick.
• Heavy cream or milk: This is optional, but it gives the soup a silky texture and tames any sharp edges from the tomatoes.
• Sharp cheddar cheese: The sharper the better for the croutons; it holds up to toasting and adds a satisfying tang.
• Sandwich bread: Plain white or whole wheat both work, just make sure the slices are sturdy enough to hold melted cheese without falling apart.
• Unsalted butter: Softened butter spreads easily and creates that golden, crispy exterior we all crave on grilled cheese.

Instructions

Prep and roast the vegetables:

Preheat your oven to 400 degrees F and arrange the halved tomatoes cut side up on a baking sheet with the onion quarters and garlic cloves. Drizzle everything with olive oil, season with salt, pepper, and thyme or basil, then roast for 25 to 30 minutes until the tomatoes are soft and their edges start to caramelize.

Simmer the soup base:

Transfer all the roasted vegetables, including any juices that collected on the pan, into a large pot with the vegetable broth, tomato paste, and sugar if you are using it. Bring everything to a gentle simmer over medium heat and let it cook for about 10 minutes, stirring now and then.

Blend until smooth:

Use an immersion blender right in the pot, or carefully transfer the soup in batches to a countertop blender, and blend until completely smooth. Stir in the cream or milk if you want a richer texture, then taste and adjust the salt and pepper as needed.

Make the grilled cheese croutons:

Butter one side of each bread slice, layer the cheese between two slices with the buttered sides facing out, then cook in a skillet over medium heat for 2 to 3 minutes per side until golden and the cheese melts. Let them cool just slightly, then cut into 1 inch cubes.

Serve hot:

Ladle the warm soup into bowls and top each serving with a handful of grilled cheese croutons. Serve immediately while the croutons are still crispy.

Save

One winter evening, my son came home from school soaked and grumpy. I heated up a bowl of this soup and floated a few grilled cheese croutons on top. He didn't say much, just ate and nodded, but later that night he asked if we could have it again the next day. That's when I realized this recipe had become more than dinner; it was comfort in a bowl.

How to Get the Best Flavor

Use the ripest tomatoes you can find, even if they are a little overripe and soft. Their sugars will caramelize during roasting and give the soup a natural sweetness that balances the acidity. If you only have less ripe tomatoes, add a pinch of sugar or a drizzle of balsamic vinegar to help round out the flavor. I have also tried adding a pinch of smoked paprika halfway through roasting, and it adds a subtle warmth that makes the soup feel almost like it came from a wood fired oven.

Making It Your Own

This recipe is forgiving and welcomes small changes. Swap the cheddar for mozzarella or Gruyere in the croutons if you want a milder or nuttier flavor. You can also skip the cream entirely for a lighter, brighter soup, or stir in a spoonful of pesto right before serving for an herby twist. I have made it with roasted red peppers mixed in with the tomatoes, and it added a gentle smokiness that my husband loved. If you are feeding a crowd, double the batch and keep it warm in a slow cooker so everyone can help themselves.

Storage and Reheating

The soup keeps well in the fridge for up to four days in an airtight container. Reheat it gently on the stovetop over low heat, stirring occasionally, and add a splash of broth or water if it has thickened too much. The grilled cheese croutons are best made fresh, but if you have leftovers, you can crisp them up again in a dry skillet for a minute or two. I do not recommend freezing the soup if you have already added cream, but the base without dairy freezes beautifully for up to three months.

• Store soup and croutons separately so the croutons stay crispy.
• Reheat individual portions in the microwave for a quick lunch.
• Make a double batch of croutons and keep them in an airtight container for up to two days.

Save

This soup has become our go to whenever someone needs a little extra warmth, whether it is a cold night or a hard day. I hope it brings the same kind of comfort to your table.

Recipe Questions & Answers

→ Can I make this soup ahead of time?

Yes, the soup keeps well in the refrigerator for up to 4 days. Reheat gently on the stovetop over low heat. Prepare the grilled cheese croutons fresh just before serving for optimal crispness.

→ What's the best way to achieve smooth texture without a blender?

An immersion blender works perfectly and creates a velvety consistency without transferring hot liquid. If you only have a countertop blender, let the soup cool slightly first, blend in batches carefully, then reheat gently.

→ How do I prevent the grilled cheese from getting soggy in the soup?

Add the croutons just before serving, or serve them on the side for guests to add themselves. This keeps them crispy and prevents sogginess from prolonged contact with hot soup.

→ Can I use canned tomatoes instead of fresh?

Yes, use high-quality canned San Marzano tomatoes. Skip the roasting step and simmer them directly in the pot with broth and aromatics for about 20 minutes, then blend as directed.

→ What cheese works best for the croutons?

Sharp cheddar offers bold flavor, but Gruyère adds sophistication, and mozzarella provides classic comfort. Choose cheeses that melt easily and have enough body to hold the bread together without excessive grease.

→ How can I make this dairy-free?

Use dairy-free butter, plant-based cheese alternatives, and coconut or oat milk instead of cream. These swaps maintain the soup's richness and the croutons' satisfying texture.