SidesMost sides finish faster than the main — start the quick ones last so everything lands hot.
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Steps
1Melt 2 tbsp butter in a large pot over medium heat. Add the onion and a pinch of salt and cook, stirring often, for 6 to 8 minutes until soft and translucent but not browned.
2Stir in the garlic and tomato paste and cook for 2 minutes, stirring constantly, until the paste darkens to a brick red and smells sweet.
3Pour in the crushed tomatoes and vegetable broth, then add the sugar. Bring to a simmer, partly cover, and cook over medium-low heat for 20 minutes, stirring now and then.
4While the soup simmers, spread the softened butter over one side of each slice of bread. Flip four slices butter-side down and lay the cheddar evenly over them, edge to edge. Top with the remaining bread, butter-side up.
5Take the soup off the heat and add the basil. Blend with an immersion blender until completely smooth, or let it cool a few minutes and blend in batches in a countertop blender, filling it no more than halfway and venting the lid.
6Return the soup to the pot over low heat and stir in the cream. Season with salt and pepper to taste, adding a little more sugar if the tomatoes taste sharp. Keep it warm on the lowest heat.
7Heat a large skillet over medium-low heat. Cook the sandwiches in batches, covered, for 3 to 4 minutes per side, pressing gently with a spatula, until the bread is deep golden and the cheese is fully melted. Lower the heat if the bread browns before the cheese melts.
8Let the sandwiches rest for 1 minute, then slice each on the diagonal. Ladle the soup into bowls and serve right away with the sandwiches alongside for dunking.