Season the beef chuck with salt and pepper. In a large pot, heat oil over medium-high heat and brown the beef for 3-4 minutes on each side. Remove and set aside.

Add more oil if needed, sauté chopped onion and celery for 5 minutes until translucent. Add minced garlic and cook for another minute.

Stir in tomato paste, cook for a minute, then add red wine, scraping the pot. Return the beef to the pot.

Add beef broth, Worcestershire sauce, thyme, and bay leaf. Boil, then reduce heat to low, cover, and simmer for 1.5 to 2 hours.

Stir in chopped carrots and potatoes, simmer uncovered for another 30 minutes until tender.

In a bowl, whisk flour, baking powder, and salt. Fold in cheddar cheese, then mix with milk and melted butter until just combined.

Drop spoonfuls of dumpling batter over the stew, cover and cook for 15-20 minutes over low heat. Broil for 2-3 minutes for a golden top if desired.

Remove the bay leaf, sprinkle parsley over the stew, and serve hot in bowls.