Warm 2 tablespoons reserved sun-dried tomato oil in a large Dutch oven or deep skillet. Add the sliced sausage and cook until lightly caramelized, about 3 minutes per side. Transfer sausage to a plate and set aside.
In the same pan, add shallot and fennel with a pinch of salt. Sauté until softened and caramelized, about 5 minutes. Sprinkle in poultry seasoning and stir to bloom, about 30 seconds. Deglaze with white wine, scraping up browned bits, and cook until the wine is fully evaporated.
Stir in garlic and chopped sun-dried tomatoes. Sauté for 2–3 minutes until fragrant.
Add penne, chicken broth, heavy cream, Parmesan rind, and black pepper. Bring to a boil, then reduce to a gentle simmer.
Cook uncovered for 15 minutes, stirring often, until the sauce reduces and turns glossy. Cover the pot and let the pasta steam for 5–8 minutes, checking and stirring once or twice, until the pasta is al dente.
Remove from the heat. Discard the Parmesan rind. Stir the sausage back into the skillet along with a generous amount of grated Parmesan. Mix until the sauce is creamy and glossy. Let rest for 2–3 minutes to thicken.
Taste and adjust seasoning. Garnish with fennel fronds and fresh basil before serving.
If your sauce reduces too quickly, covering for those final 5–8 minutes ensures the pasta finishes cooking while keeping the sauce silky.