Slice tomatoes in half and stir together with olive oil and cloves of garlic. Pour onto a roasting pan and sprinkle with salt and pepper. Roast in oven at 400°F for about 45 minutes.
Remove from oven and add contents of roasting pan into a dutch oven or large soup pot. Add in basil. Using an immersion blender, puree until smooth. If desired, you can puree in a blender (instead of using an immersion blender) and pour pureed contents into the soup pot.
Add oregano and vegetable broth and heat over low heat, covered. Simmer for about one hour, stirring occasionally.
Right before serving, add in cheese tortellini and allow to simmer for a couple of minutes. The tortellini will float on top when cooked (takes usually about 5 minutes or less).
When ready to serve, drizzle heavy cream into bowl and top with parmesan cheese! ENJOY!
Notes
Start by roasting your tomatoes and garlic with a little olive oil. Roasting brings out a deep, tangy flavor in the tomatoes and enhances the garlic aroma.
Use an immersion blender to puree the roasted tomatoes with basil. If you don’t have an immersion blender, carefully transfer the soup contents to a regular blender in batches.
Cook the soup low and slow. Give it about an hour to simmer so the flavors have a chance to mingle and combine.
Add the tortellini in the last couple of minutes. The stuffed pasta will float to the top of the soup when fully cooked. That’s how you know your soup is ready to serve!
Drizzle heavy cream into each serving bowl, then ladle in the tomato tortellini soup. Stir to combine.
Grate fresh parmesan over each serving of soup. I like to garnish with some fresh chopped basil leaves too.