Coat a large skillet with olive oil, add beef and sausage and brown until no longer pink, about 10 minutes. Season with salt and pepper.
In a food processor, combine the onion, carrots, celery, garlic, basil, parsley, an oregano. Process until pureed, add to the pan with the ground meat and stir to combine.
Mix in the flour.
Add the wine and cook until it has reduced by half, about 10 minutes
Stir in the tomatoes and pepper flakes, simmer for 10 minutes.
Stir in the heavy cream and bring back to a simmer. Sauce should be thick and coat the back of a wooden spoon.
Cook the penne in plenty of boiling salted water until pliable and barely tender, about 10 minutes.
Transfer noodles to serving bowl and toss with Extra-virgin olive oil to prevent sticking.
Top with sauce/meat mixture. Top with Gruyère and parsley.