Brown the sausage: Heat olive oil in a large, deep skillet over medium-high.
Add the sausage, breaking it up with a spoon, and cook until browned and no longer pink, 6–8 minutes. Spoon off excess fat, leaving about 1 tablespoon in the pan.
Sauté aromatics: Reduce heat to medium. Add onion and a pinch of salt.
Cook, stirring, until softened and lightly golden, 4–5 minutes. Stir in garlic and cook 30 seconds, just until fragrant.
Add sun-dried tomatoes and seasoning: Stir in sun-dried tomatoes, Italian seasoning, and red pepper flakes. Cook 1 minute to bloom the spices.
Build the sauce: Pour in crushed tomatoes and 1 cup chicken broth.
Bring to a gentle simmer and cook 3–4 minutes to meld flavors. Taste and season with salt and pepper.
Cook the tortellini: Stir in tortellini. If needed, add up to 1/2 cup more broth so pasta is mostly submerged.
Cover and simmer over medium-low, stirring once or twice, until tortellini are just tender, 4–6 minutes (check package timing).
Make it creamy: Lower heat. Stir in the heavy cream and Parmesan until smooth and silky. If sauce seems too thick, splash in a bit more broth.
If too thin, let it bubble gently for 1–2 minutes to reduce.
Add the greens: Fold in spinach and cook until just wilted, 30–60 seconds. Taste and adjust seasoning with salt and pepper.
Serve: Spoon into bowls. Top with extra Parmesan, cracked black pepper, and a drizzle of good olive oil if you like.