Brown the Beef: Season the beef chuck with salt and pepper. Heat 2 tablespoons of oil in a large pot over medium-high heat. Brown the beef in batches for 3-4 minutes on each side until caramelized, then remove and set aside.

Sauté the Aromatics: In the same pot, add diced onion and celery. Sauté for 5 minutes until translucent, then add minced garlic and cook for an additional minute.

Develop Flavor: Stir in tomato paste and cook for a minute. Pour in red wine, scraping the bottom of the pot, and simmer for 2-3 minutes.

Simmer the Stew: Return browned beef to the pot with beef broth, Worcestershire sauce, thyme, and bay leaf. Boil, then reduce heat to low, cover and simmer for 1.5-2 hours.

Add Vegetables: Stir in carrots and potatoes. Simmer uncovered for an additional 30 minutes.

Thicken if Necessary: For thicker stew, mix flour with cold water to create a slurry and stir in until thickened.

Prepare Dumplings: In a bowl, whisk together flour, baking powder, and salt. Fold in cheddar cheese and herbs, then mix in milk and melted butter gently.

Cook the Dumplings: Drop spoonfuls of batter over the stew. Cover tightly and steam dumplings for 15-20 minutes. Broil for 2-3 minutes if desired.

Serve: Remove bay leaf and ladle the stew into bowls, garnishing with fresh parsley before serving.