Cook the penne pasta as directed on the package, saving one cup of the pasta water before draining. Place the drained pasta back into the cooking pot.
While the pasta cooks, warm a large non-stick skillet over medium heat and add the ground beef. Sprinkle with salt and Italian seasoning. Let it brown undisturbed for 4 to 5 minutes to develop a crust, then break it up and stir.
Continue cooking the beef until no pink remains, around 3 to 5 more minutes. Drain excess fat if you prefer.
Add the chopped onion and minced garlic to the skillet with the beef. Stir occasionally and cook until the onions soften, about 3 to 4 minutes.
Mix in the tomato paste and Worcestershire sauce thoroughly. Then pour in the diced tomatoes with their juices and cook for 1 to 2 minutes until heated through.
Pour in the heavy cream and stir for about 30 seconds to combine, then sprinkle over the shredded Cheddar cheese and stir until melted completely.
Transfer the beef mixture to the pot with the cooked pasta. Stir everything together well.
Add 2 to 4 tablespoons of the reserved pasta water to the pot to loosen the sauce and give it a smooth texture. Adjust seasoning with salt and pepper if desired.