Season beef with 1 teaspoon salt and pepper. Heat oil in a Dutch oven and brown the beef in batches, then set aside. Cook onion for 7 minutes and garlic for 1 minute.
Deglaze with wine. Add tomatoes, 2 cups stock, cinnamon, bay leaves, oregano, and beef. Cover and simmer gently for 75 to 90 minutes until nearly tender.
Bake with Orzo:
Heat the oven to 375 F (190 C). Remove cinnamon and bay leaves. Transfer beef and sauce to a shallow casserole, stir in orzo, remaining stock, and remaining salt.
Bake uncovered for 25 to 30 minutes, stirring once and adding hot water if needed, until the orzo is tender and saucy. Rest for 10 minutes.
Finish:
Spoon into warm plates and finish lightly with grated cheese and parsley.
Notes
Keep extra hot water nearby because orzo absorption varies by brand.
Refrigerate for up to three days; loosen with stock or water when reheating.