Roasted Tomato Soup with Grilled Cheese

My daughter used to refuse tomato soup until she watched me dunk a grilled cheese into a steaming bowl one rainy Saturday. She grabbed the sandwich right out of my hand, dipped it herself, and declared it magic. Now she asks for it every time the weather turns gray. This recipe takes that same childhood magic and turns it into something a little more grown-up, roasting the tomatoes until they're sweet and smoky, then topping each bowl with crispy, golden croutons that melt into the soup as you eat.

I made this for a small dinner party once, and my friend who claimed she hated cooked tomatoes had three bowls. She kept fishing out the croutons with her spoon like little treasures. By the end of the night, she was asking if I could teach her how to roast vegetables because she had no idea it could taste like that. It became my go-to whenever I want to impress someone without actually working that hard.

Ingredients

• Ripe tomatoes: Use the ripest, reddest ones you can find because roasting concentrates everything, including bland flavor if theyre not good to start with.
• Onion and garlic: These roast alongside the tomatoes and turn sweet and jammy, adding a base layer of flavor that makes the soup taste complex.
• Olive oil: Dont skimp here because it helps everything caramelize and adds a silky richness to the final soup.
• Dried thyme or basil: I usually go with thyme in the fall and basil in the summer, but either works beautifully with tomatoes.
• Vegetable broth: This thins the soup to the right consistency and adds a savory backbone without overpowering the tomato flavor.
• Tomato paste: Just a tablespoon deepens the color and adds an extra layer of umami that makes the soup taste richer.
• Sugar: A tiny bit balances the acidity if your tomatoes are tart, but taste first because you might not need it.
• Heavy cream or whole milk: This is optional, but it makes the soup velvety and a little more indulgent if youre in the mood.
• Sandwich bread: I like a sturdy white or sourdough that crisps up well and holds the cheese without falling apart.
• Sharp cheddar cheese: The sharper the better because it adds a punch of flavor that stands up to the sweetness of the soup.
• Unsalted butter: Softened butter spreads easily and gives the croutons that perfect golden crust.

Instructions

Preheat and prep:

Set your oven to 400°F and line a baking sheet with parchment if you want easy cleanup. Halve the tomatoes and arrange them cut side up so they roast evenly and get those caramelized edges.

Season and roast:

Toss the tomatoes, onion, and garlic with olive oil, salt, pepper, and herbs right on the sheet. Roast for 25 to 30 minutes until the tomatoes are soft, jammy, and starting to brown at the edges.

Simmer the soup:

Scrape everything into a large pot, including the sweet, sticky juices from the pan. Add broth, tomato paste, and sugar if using, then simmer for 10 minutes to let the flavors marry.

Blend until smooth:

Use an immersion blender right in the pot, or carefully transfer to a countertop blender in batches. Blend until silky, then stir in cream or milk if you want it richer.

Make the croutons:

Butter the outside of each bread slice, layer cheese in the middle, and grill in a hot skillet until golden and melty, about 2 to 3 minutes per side. Let them cool just enough to handle, then cut into bite-sized cubes.

Serve hot:

Ladle the soup into bowls and pile the grilled cheese croutons on top. They soften as they sit, so serve immediately for the best texture contrast.

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One winter evening, my son came home from college unannounced, cold and tired. I had a pot of this soup on the stove and a loaf of bread on the counter. We didnt say much, just sat at the kitchen table dunking croutons and listening to the radiator clank. He told me later that it was the first time in months he felt like he could exhale. Food has a way of doing that when you least expect it.

How to Store and Reheat

The soup keeps beautifully in the fridge for up to four days in an airtight container, and it actually tastes better the next day after the flavors settle. Reheat it gently on the stove over low heat, stirring occasionally, and add a splash of broth or water if it thickens too much. The croutons, however, are best made fresh because they lose their crunch quickly, but you can prep the sandwiches ahead and grill them right before serving.

Customizing Your Soup

Ive added roasted red peppers when I had them on hand, and theyve added a subtle sweetness that plays well with the tomatoes. A pinch of smoked paprika or a swirl of pesto right before serving can take this in a completely different direction if youre feeling adventurous. Some people love a kick of red pepper flakes, and I wont argue because it adds a warmth that feels especially good on cold nights.

Pairing and Serving Ideas

This soup is filling enough to be the main event, especially with the croutons, but it also works as a starter before something lighter like roasted chicken or a big salad. I like serving it with extra crusty bread on the side for anyone who wants to keep dunking. A crisp green salad with a sharp vinaigrette cuts through the richness and makes the whole meal feel balanced.

• Try garnishing with fresh basil or a drizzle of good olive oil for a restaurant-style finish.
• Swap the cheddar for Gruyère or fontina if you want a more sophisticated flavor in the croutons.
• If youre feeding a crowd, set up a toppings bar with croutons, herbs, and cream so everyone can customize their bowl.

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This soup has become my answer to almost every kind of day, whether its a celebration, a comfort, or just a Tuesday. I hope it finds a place in your kitchen the way it has in mine.

Recipe Questions & Answers

→ Can I make this soup ahead of time?

Yes, the soup keeps well in the refrigerator for up to 3 days. Store in an airtight container. Reheat gently on the stovetop over medium-low heat, adding a splash of broth if needed. Prepare croutons fresh for best crispness, or store them separately in an airtight container for up to 2 days.

→ What's the best way to achieve perfectly roasted tomatoes?

Cut tomatoes in half, place cut-side up on the baking sheet, and roast at 400°F for 25–30 minutes until deeply caramelized. The key is allowing the natural sugars to concentrate. Don't crowd the pan, and let them sit undisturbed for even browning.

→ How do I get creamy soup without heavy cream?

Use whole milk or even a combination of milk and broth for a lighter version. For a vegan option, try unsweetened oat milk or cashew cream. You can also blend in a portion of roasted vegetables for natural creaminess without dairy.

→ Can I use canned tomatoes instead of fresh?

Yes, use two 28-ounce cans of high-quality crushed or whole tomatoes. Drain excess liquid before roasting. Note that fresh tomatoes provide superior depth when caramelized, but canned works well in cooler months when quality fresh tomatoes aren't available.

→ What cheese works best for the croutons?

Sharp cheddar provides excellent flavor and melts beautifully. For variation, try Gruyère for earthiness, aged Gouda for sweetness, or fontina for a creamy melt. Avoid soft cheeses that won't hold their shape when cubed.

→ How do I prevent the grilled cheese from burning?

Medium heat is essential—this allows cheese to melt while bread toasts evenly. Use softened butter for even application, and watch carefully during cooking. If edges brown too quickly, reduce heat slightly and increase cooking time. The goal is golden brown bread with fully melted cheese.