Bring a large pot of salted water to a boil and add the penne, stirring occasionally. While the pasta cooks, mince the garlic and chop the sun-dried tomatoes into 1/4-inch strips. Measure out the cream, wine, tomato paste, and have the oregano and red pepper flakes ready. The pasta should take about 9-11 minutes to reach al dente; timing it to finish around the same time as your sauce will create the best final dish.
Heat a large skillet over medium-high heat. Remove the sausage from its casings and crumble it directly into the pan, breaking it into small, bite-sized pieces as it cooks. Let it cook undisturbed for 2-3 minutes to develop color, then stir and continue cooking for another 3-4 minutes until the meat is browned and cooked through. Transfer the cooked sausage to a plate, leaving about 1 tablespoon of the fat in the pan for building flavor.
In the same skillet with the reserved sausage fat, add the minced garlic and sauté for 30 seconds until fragrant. Pour in the white wine and let it simmer for 1-2 minutes, scraping up any browned bits from the bottom of the pan. This deglazing step captures all the savory flavors left behind from the sausage—I never skip it because it's where so much of the dish's depth comes from.
While the wine is reducing, whisk together the cornstarch and 2 teaspoons of water in a small bowl until smooth—this slurry will thicken the sauce beautifully without lumps. Reduce the heat to medium and pour the heavy cream into the skillet. Add the tomato paste, sun-dried tomatoes, oregano, and red pepper flakes, stirring well to combine. Then slowly whisk in the cornstarch slurry while stirring constantly, cooking for 1-2 minutes until the sauce thickens and becomes glossy.
Return the browned sausage from Step 2 to the skillet and stir it into the cream sauce. Let everything simmer together for 1-2 minutes to meld the flavors. Taste the sauce and season with kosher salt and freshly ground black pepper. I like to add just a tiny pinch of extra salt to make the richness really sing, but go easy—the pasta water and cheese will add saltiness too.
Drain the cooked penne from Step 1 and add it directly to the skillet with the sausage cream sauce. Toss everything together until the pasta is evenly coated, about 1 minute. Divide the pasta among serving bowls, top with torn fresh basil and additional grated parmesan cheese, and serve immediately while the sauce is still creamy and warm.