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Heat 1 tablespoon of olive oil in a large pot or Dutch oven over medium heat.

Add the diced onion to the pot and sauté until softened and translucent, about 5-7 minutes.

Add the minced garlic to the pot and sauté for another minute until fragrant.

Pour the 28 ounces of crushed tomatoes into the pot. Stir in the 1 teaspoon of sugar, 1/2 teaspoon of salt, and 1/4 teaspoon of black pepper.

Bring the soup to a simmer, then reduce heat to low, cover, and let it cook for 10-15 minutes to allow the flavors to meld.

Carefully blend the soup using an immersion blender until it is smooth. Alternatively, transfer in batches to a regular blender (be cautious with hot liquids) and blend until smooth, then return to the pot.

Stir in the 1/2 cup of heavy cream until fully combined. Keep the soup warm over low heat while preparing the grilled cheese.

For each grilled cheese sandwich: Spread 1 tablespoon of mayonnaise evenly on one side of a slice of sourdough bread. This will be the outside of the sandwich.

Place 2 slices of cheddar cheese on the un-mayonnaised side of the same slice of bread. Top with another slice of sourdough bread.

Spread 1 tablespoon of mayonnaise evenly on the top slice of bread. Repeat for all four sandwiches.

Melt 1 tablespoon of butter in a large non-stick pan or griddle over medium heat. Place one or two sandwiches (depending on pan size) in the pan, mayonnaise-side down.

Cook until the bottom slice is golden brown and crispy, about 3-4 minutes.

Flip the sandwich and cook the other side until golden brown and the cheese is melted and gooey, another 3-4 minutes. Repeat for remaining sandwiches, adding butter as needed for each batch.

Once cooked, remove the grilled cheese from the pan and cut each sandwich diagonally.

Ladle the warm tomato soup into bowls. Garnish with fresh basil, if desired. Serve immediately alongside the grilled cheese sandwiches.


Heat 1 tablespoon of olive oil in a large pot or Dutch oven over medium heat.

Add the diced onion to the pot and sauté until softened and translucent, about 5-7 minutes.

Add the minced garlic to the pot and sauté for another minute until fragrant.

Pour the 28 ounces of crushed tomatoes into the pot. Stir in the 1 teaspoon of sugar, 1/2 teaspoon of salt, and 1/4 teaspoon of black pepper.

Bring the soup to a simmer, then reduce heat to low, cover, and let it cook for 10-15 minutes to allow the flavors to meld.

Carefully blend the soup using an immersion blender until it is smooth. Alternatively, transfer in batches to a regular blender (be cautious with hot liquids) and blend until smooth, then return to the pot.

Stir in the 1/2 cup of heavy cream until fully combined. Keep the soup warm over low heat while preparing the grilled cheese.

For each grilled cheese sandwich: Spread 1 tablespoon of mayonnaise evenly on one side of a slice of sourdough bread. This will be the outside of the sandwich.

Place 2 slices of cheddar cheese on the un-mayonnaised side of the same slice of bread. Top with another slice of sourdough bread.

Spread 1 tablespoon of mayonnaise evenly on the top slice of bread. Repeat for all four sandwiches.

Melt 1 tablespoon of butter in a large non-stick pan or griddle over medium heat. Place one or two sandwiches (depending on pan size) in the pan, mayonnaise-side down.

Cook until the bottom slice is golden brown and crispy, about 3-4 minutes.

Flip the sandwich and cook the other side until golden brown and the cheese is melted and gooey, another 3-4 minutes. Repeat for remaining sandwiches, adding butter as needed for each batch.

Once cooked, remove the grilled cheese from the pan and cut each sandwich diagonally.

Ladle the warm tomato soup into bowls. Garnish with fresh basil, if desired. Serve immediately alongside the grilled cheese sandwiches.
