Heat olive oil in a large pot over medium heat. Add crumbled Italian sausage and cook until browned, about 5–7 minutes. Remove sausage and set aside.

In the same pot, add diced onion and minced garlic to the drippings. Sauté for 3–4 minutes until onion is soft and garlic is fragrant.

Stir in drained diced tomatoes, chicken stock, oregano, and dried basil. Bring to a simmer over medium-high heat for about 10 minutes.

Add ditalini pasta to the simmering broth. Cook for about 8–10 minutes, stirring occasionally until pasta is al dente.

Reduce heat to low, gently stir in heavy cream and freshly grated Parmesan cheese. Keep stirring until cheese melts, about 2–3 minutes. Adjust seasoning with salt and pepper.

Ladle soup into bowls and garnish with chopped parsley. Serve immediately with crusty bread.