Brandied Cranberry Short-Rib Stew

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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

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