Heat 1 tablespoon oil in a large, oven-safe pot over medium-high heat. Season the beef with salt and pepper and brown, about three minute, cooking in batches if needed. Remove the beef to a bowl.
Heat the remaining oil in the pot, add the onion and garlic and cook for 5 minutes, or until softened. Add the paprika and chipotles and cook for 1 minute. Return the beef to the pan along with the brown sugar, tomato paste, cherry tomatoes, and stock, and bring to the boil. Reduce heat to low and cover with a tight-fitting lid. Cook for 3–3½ hours or until tender.
Preheat oven 400 degrees F.
Combine all dumpling ingredients in a bowl and mix to combine. Spoon onto the beef and bake, uncovered, for 15–20 minutes or until cooked through and golden. Serve hot.