Preheat oven to 400 degrees F (205 degrees C). Fully line two rimmed baking pans with parchment paper.
Arrange the Plum Tomato (3 pound), Onion (1), cut lengthwise into 8 wedges, and Red Bell Pepper (1/2 cup) in a single layer on the lined baking pans.
Drizzle the Olive Oil (3 tablespoon) over the tomato mixture. Season with the Kosher Salt (1 1/2 teaspoon) and Freshly Ground Black Pepper (1 teaspoon).
Roast the tomato mixture in the preheated oven for 30 minutes.
Add the Garlic (3 clove). Continue roasting until the mixture is tender, an additional 15 minutes.
Meanwhile, bring Chicken Broth (5 cup) to a boil in a large pot or dutch oven. Reduce heat and simmer, covered.
Transfer the roasted veggies directly to the hot broth.
Using an immersion blender, process until the entire mixture is smooth.
Simmer for 5 minutes, until heated through.
Stir in the Fresh Basil (2 tablespoon) and Fresh Parsley (2 tablespoon). For a creamier consistency, add Half and Half (to taste). You can also serve the soup as it is with the cream on the side to be added, if desired, to individual servings.
Top with Croutons (to taste). Serve and enjoy!