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Export 8 ingredients for grocery delivery
Step 1
Make the soup: Dump the canned tomatoes and their juices into a medium pot and using your hands, tear into coarse chunks. Swish the broth in the empty tomato can and add to the pot.
Step 2
Stir in the onion, butter, oregano and sugar and season generously with salt and pepper. Turn the heat to high and bring to a simmer. Reduce the heat to medium-low, cover and continue simmering, stirring occasionally, until the onion is tender and the tomatoes have broken down, 15 to 20 minutes.
Step 3
Meanwhile, make the sandwiches: Spread a thin layer of mayonnaise on one side of each slice of bread and evenly sprinkle the cheese and a little oregano on the mayonnaise side of 4 slices. Top with the cheeseless slices, mayonnaise-side down.
Step 4
Melt 1 tablespoon butter in a large skillet over medium. Add the sandwiches and cook until golden brown on the bottoms, 2 to 3 minutes. Melt the remaining tablespoon of butter in the pan, then flip the sandwiches with a spatula, move them around to coat with the butter and cook until the other side is golden brown and the cheese is melted, 1 to 2 minutes. Turn heat to lowest setting to keep sandwiches warm.
Step 5
Carefully purée the tomato soup using a blender until smooth and creamy, adding more broth if needed to loosen to your desired consistency. Season with salt and pepper. Transfer the grilled cheeses to a cutting board and cut each in half diagonally. Serve alongside the soup.