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Heat olive oil in a large pot over medium heat. Add Italian sausage, breaking it apart with a spoon. Cook until browned and no longer pink, about 5-6 minutes.
Add diced onion and cook until softened, around 3 minutes. Stir in the minced garlic and cook for another 30 seconds until fragrant.
Pour in the drained diced tomatoes, chicken broth, dried basil, and oregano. Stir well and bring to a gentle simmer.
Add the ditalini pasta, cover, and cook for 8–10 minutes, until pasta is just tender.
Lower the heat and stir in heavy cream and Parmesan cheese. Mix well until the cheese is melted and the soup is luscious and creamy.
Taste and season with salt and pepper as needed.
Ladle into bowls and top with fresh parsley and an extra sprinkle of Parmesan before serving.