Preheat oven to 400 Degree F.
In a large cast-iron stockpot or heavy bottom saucepan
Cook bacon over medium-high heat until crisp. Remove bacon from pan and drain on a paper-lined plate for 10 minutes.
To make bacon dust: pulse bacon in a coffee mill until it resembles fine dust. Set aside
Sauté the garlic in the bacon fat for 30 seconds, add sliced cherry tomatoes and cook for 3 minutes, stirring to combine.
Add both cans of seasoned tomatoes as well as, sundried tomatoes and water. Bring to a boil. Reduce heat and cook for 25-30 minutes. Remove from heat. Using an immersion blender, pulse the mixture until smooth. Add ¼ cup heavy cream and stir to combine. Keep soup warm
While the soup is simmering; cut bread into cubes. Drizzle with 2 tablespoons olive oil, garlic salt, parmesan cheese, 1 tablespoon fresh chiffonade of basil, and fresh black pepper. Toss to combine. Evenly spread seasoned bread onto a baking sheet. Drizzle with remaining olive oil and bake at 400 degrees F. for 10 minutes. Remove from oven and sprinkle with bacon dust reserving some dust for garnish. Bake for additional 5 minutes or until golden brown. Keep bacon croutons at room temperature until ready to plate the soup.