In a stock pot or dutch oven, heat olive oil over medium-high heat. Add garlic and saute for 30 seconds. Add onion and cook, stirring as needed, until translucent.
Add tomatoes (do not drain), stock, and sugar. Bring to a low simmer. Cook uncovered for 10 minutes or until slightly thickened.
Add the half & half, basil, oregano, red pepper flakes and salt/pepper.
Using an immersion blender, puree soup until smooth. You can also place into a regular blender, being careful since soup will be very hot.
Stir in parmesan cheese and serve topped with buttery croutons.