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In a 3- to 4-quart saucepan, melt butter over medium-high heat, then add onions. Cook, stirring, until onions are tender and beginning to brown at edges, about 5 to 7 minutes.
Add garlic and cook for 1 minute.
Add tomato paste, and cook for 2 to 3 minutes.
Add sherry, if using, and cook for 1 minute, then add tomatoes. Cook the tomatoes, mashing them slightly with your spoon, for 3 minutes.
Add broth and seasoning to taste — start with 1 teaspoon kosher salt, many grinds of black pepper, and a couple pinches of pepper flakes.
Bring mixture to a simmer and cover the pot. Cook at a simmer for 15 to 20 minutes.
Blend the hot soup carefully until totally smooth.
Taste, adjust seasoning as needed. If you’d like the soup to be creamy, add cream a splash at a time, stirring, until you reach your desired level.
Add sherry vinegar for brightness at the end, if desired.
Ladle into bowls or mugs, finish with freshly ground black pepper, and serve with grilled cheese fingers.