Heat a large heavy pot to medium heat with 2 tablespoons of olive oil and add the sausage. Cook the sausage until browned while breaking it up into small pieces. Once brown, remove the sausage with a slotted spoon to a plate and set aside.
To the pot, add the remaining olive oil along with the onion, celery, carrot, fennel seeds, and a pinch of salt. Cook until soft while stirring every so often (about 7-10 minutes). Add the garlic and cook for another 2 minutes or until fragrant.
Add the tomato paste and cook stirring frequently for 5 minutes. If the paste starts to burn lower the heat and add a touch of water to the pot.
Add the flour and cook for 2 minutes, stirring constantly. Next, add the wine and turn the heat to high. With a wooden spoon scrape the bottom of the pot to dislodge any browned bits. Once the wine has reduced by half (about 1-2 minutes) add the cooked sausage, chicken stock, and Parmigiano rind. Bring to a boil.
Once boiling, lower the heat and simmer for 10 minutes. Add the cream and simmer the soup for another 10 minutes.
Add the tortellini and cook until tender (about 3-5 minutes) then remove the pot from the heat. Taste test the soup and adjust salt and pepper if required. Stir in the parsley and basil.
Serve in bowls with grated cheese and crusty bread. Enjoy!