Season the beef chuck with salt and pepper, then heat a drizzle of oil in a large pot over medium-high heat. Brown the beef in batches for about 5-7 minutes per side until richly caramelized.

Once the beef is browned, add oil if needed and sauté the chopped onion and celery in the same pot for 4-5 minutes until softened. Stir in minced garlic and cook for an additional minute until fragrant.

Stir in the tomato paste, then pour in the red wine to deglaze the pot. Scrape up any flavorful bits. Return the beef to the pot, add beef broth, Worcestershire sauce, thyme, and bay leaf. Bring to a boil, then reduce to low heat and simmer for 1.5 to 2 hours until tender.

After the beef has simmered, stir in the chopped carrots and diced potatoes. Continue to simmer uncovered for another 30 minutes until the vegetables are fork-tender.

Mix flour with a splash of cold water to create a slurry. Stir this mixture into the simmering stew, allowing it to thicken for an additional 5-10 minutes.

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

Drop spoonfuls of dumpling batter on top of the simmering stew. Cover and cook for 15-20 minutes over low heat until the dumplings are puffed and cooked through.

Remove and discard the bay leaf. Ladle the beef stew into bowls, sprinkle fresh parsley on top, and serve hot.