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Preheat oven to 400°F. Add 1/2-inch water to the bottom of a large roasting pan. Arrange the squash halves, cut sides down, in the roasting pan. Bake, uncovered, for 30 minutes. Turn squash halves cut sides up. Brush cut sides of squash with 2 tablespoons of the melted butter. Sprinkle with brown sugar, salt, and pepper. Bake, uncovered, for 20 to 25 minutes more or just until tender.
Meanwhile, in a large skillet cook and stir pancetta over medium heat for 5 to 6 minutes or until crisp. Using a slotted spoon, remove pancetta from skillet. Drain on paper towels.
Add onion to drippings in skillet; cook and stir for 4 to 5 minutes or until onion is tender. Add spinach, sage, and the crisped pancetta. Cook and stir for 2 minutes or until spinach wilts. Remove skillet from heat. Stir in the cooked rice, pecans, and cranberries. Mix well.
Divide rice mixture among squash halves, filling each cavity with about 2/3 cup rice mixture. Drizzle with remaining melted butter. Bake, uncovered, for 20 to 25 minutes more or until heated through.