Sear the Beef: Season beef chuck generously with salt and pepper. Heat a tablespoon of oil over medium-high heat. Brown the beef in batches for about 3-4 minutes on all sides. Remove beef and set aside.

Sauté Aromatics: In the same pot, add another tablespoon of oil if needed. Sauté chopped onion and diced celery for about 5 minutes until softened. Add minced garlic and cook for an additional 30 seconds until fragrant.

Build the Stew Base: Stir in tomato paste, cooking for about 2 minutes. Pour in red wine to deglaze, scraping the pot. Return beef to the pot with beef broth, Worcestershire sauce, thyme, and bay leaf. Bring to a boil, then simmer covered for 1.5 to 2 hours.

Add Vegetables: Stir in diced carrots and cubed potatoes once beef is tender. Simmer uncovered for an additional 30 minutes.

Prepare Dumplings: Combine flour, baking powder, and a pinch of salt in a bowl. Mix milk and melted butter in another bowl, then fold into dry ingredients with shredded cheddar cheese.

Dumpling Cooking: Drop spoonfuls of the batter onto the stew. Cover and let cook for 15-20 minutes. For a golden top, place the pot under a broiler for 2-3 minutes.

Serve: Remove from heat and discard bay leaf. Garnish with chopped parsley. Serve hot in bowls.