Brown the sausage by heating olive oil in a large pot over medium heat. Add the Italian sausage, breaking it apart with a spoon as it cooks until browned all over. Remove it from the pot and set aside while leaving some drippings behind.
In the same pot, add the diced onion and minced garlic. Sauté until they become soft and fragrant, about 3–4 minutes.
Stir in the drained diced tomatoes along with the chicken stock, dried basil, and oregano. Return the browned sausage back into the pot and bring everything to a gentle simmer for about 10 minutes.
Add in the ditalini pasta and cook until it's al dente, usually around 8–10 minutes depending on package instructions.
Lower the heat and stir in heavy cream and freshly grated Parmesan cheese. Mix well until both are fully melted into a creamy consistency.
Taste the soup and season with salt and freshly cracked black pepper according to preference. Garnish with fresh parsley before serving hot.