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In a food processor combine peppers, tomatoes, broth, olive oil, tarragon, celery seed, garlic, and sugar. over and process half at a time if necessary, to desired consistency. Season to taste with salt and pepper; set aside.
For Pepperoni Cheese Toast, brush one side of each bread slice with mayonnaise. Layer pepperoni and cheese on the unbrushed sides of 4 slices. Top with remaining bread slices, mayonnaise side up. On a large griddle or skillet toast sandwiches over medium heat until cheese is melted and bread is golden, turning once, about 3 to 5 minutes.
Divide soup among bowls; top with cucumber. Sprinkle with crushed red pepper and olive oil, if desired. Serve with Pepperoni Cheese Toasts.