6 pounds bone-in beef short ribs, cut into 2-in. pieces
About 2 tsp. kosher salt, divided
About 1 tsp. black pepper
3 tablespoons vegetable oil, divided
3 pounds kabocha squash (1 small), seeded, cut into 2-in. wedges, and peeled
2 medium onions, finely chopped
1/3 cup flour
4 garlic cloves, minced
3 tablespoons Dutch-processed bittersweet cocoa powder or 1 square (1 oz.) bittersweet chocolate, chopped
5 cups reduced-sodium beef broth
1/2 cup brandy
1/2 cup dried cranberries
2 tablespoons minced candied ginger
1 tablespoon finely shredded orange zest
1 1/2 cups fresh cranberries
1. Preheat oven to 500°. Dry short ribs on paper towels and sprinkle with 1 tsp. each salt and pepper. In a large, heavy ovenproof pot, heat 1 tbsp. oil over medium-high heat. In 4 batches, brown ribs all over. Transfer to a bowl.
2. Cut squash wedges crosswise, put on a baking sheet, and toss with remaining oil. Roast until caramelized, 10 minutes. Remove from oven and lower heat to 300°.
3. Add onions and remaining 1 tsp. salt to pot and cook over medium-high heat, stirring often, until softened, about 3 minutes. Add flour and cook, stirring, until deep golden brown, about 5 minutes. Stir in garlic and cocoa; cook 1 minute. Stir in broth and brandy. Add dried cranberries, ginger, and orange zest and bring mixture to a boil. Return short ribs to pot, cover, and bake 2 1/2 hours.
4. Remove pot from oven and spoon off fat. (Or chill overnight before skimming; return to a simmer before continuing.) Stir in fresh cranberries and kabocha. Cover and bake until kabocha is tender and meat pulls away from the bone, about 30 minutes.