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Preheat oven to 400.
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Place the acorn squash on a baking pan lined with parchment paper. Drizzle with 1 Tbsp olive oil and season with salt and pepper. Bake 25 minutes.
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Heat the remaining oil in a large pan over medium heat. Add the onion, sage, and basil. Stir in the garlic and sausage and cook until sausage is slightly browned.
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Add the apple and cook until it is soft.
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In a baking dish, add the acorn squash and sausage mixture.
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Stir in the breadcrumbs and cheese. Top with additional cheese and bake 15 minutes.