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PREHEAT oven to 350°F. Cut squash crosswise into 1-inch-thick slices; arrange in single layer in 15x10x1-inch baking pan. Melt 2 Tbsp. of the butter; brush onto squash slices. Cover. Bake 15 minutes.
CUT remaining 1/4 cup butter into small pieces; place in medium bowl. Drain pineapple, reserving pineapple and juice separately. Add enough hot water to reserved pineapple juice to measure 1-1/2 cups. Add to pineapple mixture; stir until butter is melted. Add stuffing mix, pineapple, pecans, raisins, green onion and pepper; stir just until moistened. Spoon evenly over squash slices.
BAKE an additional 20 minutes or until squash is tender and stuffing mixture is heated through.