Cut the beef chuck into 1-inch cubes and season with salt and pepper. In a large heavy pot or Dutch oven, heat a tablespoon of oil over medium-high heat. Brown the beef in batches for about 5-7 minutes until well-seared. Transfer to a plate.

In the same pot, reduce the heat to medium, and add diced onion and celery. Sauté for about 5 minutes until softened. Stir in minced garlic and cook for an additional minute.

Add tomato paste to the pot, stirring for about 1 minute to enrich the flavors and improve the base color.

Pour in red wine and scrape up browned bits from the pot. Allow to simmer for about 2 minutes until slightly reduced, then return the beef to the pot.

Add beef broth, Worcestershire sauce, thyme, and a bay leaf. Bring to a boil, then reduce heat to low. Cover and simmer for 1.5 to 2 hours.

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

If needed, mix a tablespoon of flour with 2 tablespoons of cold water to create a slurry and stir into the stew.

In a mixing bowl, whisk together flour, baking powder, salt, and chopped fresh herbs. Fold in cheddar, milk, and melted butter until just combined.

Drop spoonfuls of the dumpling batter over the simmering stew and cover the pot. Steam dumplings for 15-20 minutes, then broil for 2-3 minutes if a golden top is desired.

Remove the bay leaf, serve stew in bowls topped with dumplings, and sprinkle with fresh parsley.