Begin by patting the chuck roast cubes dry and seasoning them generously with salt and black pepper. In a large Dutch oven, heat a splash of olive oil over medium-high heat. Carefully add the beef in batches, searing each side for 3-4 minutes until beautifully caramelized.

Once all the meat is browned, reduce the heat to medium and add the chopped onions. Sauté for about 5 minutes until softened.

Add minced garlic, thyme, rosemary, and tomato paste, cooking for another 2 minutes until fragrant.

Pour in the Guinness and deglaze the pot, scraping up the flavorful browned bits. Simmer for about 3 minutes to let the alcohol evaporate.

Return the browned beef, add beef stock and bay leaves, and stir. Bring to a simmer and cover before baking for 1.5 hours at 325°F.

After 1.5 hours, stir in carrots, potatoes, celery, mushrooms, and remaining Guinness. Bake covered for an additional 1.5 hours.

While the stew bakes, prepare cheddar dumplings by mixing Bisquick, garlic powder, cheddar cheese, and chives. Stir in milk until a thick dough forms.

Once the stew is done, drop spoonfuls of dough on the simmering broth, cover, and steam for 10 minutes, then uncover and cook for another 10 minutes.

Let the stew rest for 15-30 minutes before serving.