Preheat oven to 350 degrees F.

Heat 1 1/2 teaspoons oil in a large ovenproof saucepan over medium heat. Add beef and cook until browned on all sides, 6 to 8 minutes. Transfer to a plate.

Reduce heat to medium-low, add the remaining 1 teaspoon oil and shallot to the pan; cook, stirring often, for 1 minute. Stir in thyme, sage, salt and pepper; cook for 30 seconds. Return the beef to the pan and sprinkle with flour. Cook, stirring often, until the flour browns, about 3 minutes. Pour in broth; scrape up any browned bits from the bottom of the pan. Continue cooking until the liquid bubbles and thickens slightly, about 2 minutes. Stir in squash.

Cover the pan and transfer to the oven. Bake for 1 hour. Stir in cherries, cover and continue baking until the meat is tender when pierced with a fork, about 30 minutes more. Makes 2 servings, about 1 1/2 cups each.