Begin by seasoning the beef chuck with salt and pepper. Heat oil in a large pot over medium-high heat until shimmering. Add beef pieces and sear until browned on all sides, about 8-10 minutes.

In the same pot, add chopped onion and celery, sautéing for about 5 minutes. Then, add minced garlic and cook for an additional 1 minute.

Stir in tomato paste, letting it cook for 1-2 minutes. Deglaze the pot with red wine, scraping up browned bits and let cook for about 3 minutes until the wine reduces.

Return the seared beef to the pot, and pour in enough beef broth to cover the meat. Add Worcestershire sauce, fresh thyme, and a bay leaf. Bring to a boil, then reduce to low and let simmer for 1.5 to 2 hours.

Add chopped carrots and potatoes to the pot, stir well, and continue to simmer uncovered for 30 minutes.

Prepare the Cheddar Herb Dumplings by combining flour and baking powder in a bowl. Fold in shredded cheddar and chopped herbs, then pour in milk and melted butter, mixing gently.

Drop spoonfuls of the dumpling batter onto the bubbling stew. Cover the pot and cook for 15-20 minutes until the dumplings are cooked through.

Once done, ladle the stew into bowls and garnish with fresh parsley before serving.