Preheat oven to 450 degrees Fahrenheit and line a baking sheet with aluminum foil.
Strain the whole tomatoes (keep the liquid) and remove the seeds from the tomatoes as the liquid strains.
Place the seeded tomatoes onto the baking sheet. Sprinkle the tomatoes with the light brown sugar. Put the baking sheet into the oven and roast the tomatoes for 30 minutes (or until the tomatoes lightly char).
In a large soup pot over medium-high heat, melt the butter, then add the onion. Sauté the onion in the butter until translucent (approximately 5 minutes).
To the soup pot add the flour, tomato paste, cayenne pepper powder, and salt. Stir to aromatic (one minute).
Add the chicken broth to the soup pot and stir to combine with the butter/onion mix. Simmer the chicken broth for 4 to 5 minutes.
Add the tomato juice from the canned whole tomatoes and stir to combine. Bring the liquid to a boil, then lower heat to medium to simmer.
Add the roasted tomatoes to the liquid and stir to combine. Continue simmering the soup for 15 to 20 minutes, until the liquid has slightly thickened.
Using a hand blender, blend the tomatoes to smooth in the soup, then turn the heat to low and add the apple juice and cream. Simmer for 2 to 3 minutes, stirring occasionally.
Ladle the soup into bowls then top with croutons. OPTIONAL: Sprinkle a dash of cayenne pepper powder atop the soup for additional color and heat.