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Heat the oil in a dutch oven over medium-high heat. Add the onion, celery and carrots and cook about 5 minutes, stirring occasionally. Stir in the garlic and cook 30 seconds or until fragrant.
Add the tomatoes(and juice from the can), vegetable broth, water, lentils, bay leaves, basil, oregano and ½ tsp salt. Stir to combine and bring to a boil.
Reduce heat to low, cover and simmer for about 1 hour. Add salt and pepper to taste.
Preheat oven to 450°F. Place a slice of cheddar between 2 slices of bread to make 3 sandwiches. Butter the outer slices of bread on each sandwich evenly with the butter.
Place sandwiches on a baking sheet and place in the preheated oven. Bake for 8 minutes then flip the sandwiches and bake an additional 5 minutes or until desired crispiness.
Allow sandwiches to cool 5 minutes then cut into small squares and serve on top of the soup.