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Preheat oven to 400°. On a large baking sheet, rub insides of spaghetti squash with olive oil and season generously with salt and pepper. Bake until tender, 55 minutes to 1 hour. Remove from oven and heat broiler. Once cool enough to handle, shred spaghetti squash with a fork. Meanwhile, in a large skillet over medium-high heat, cook sausage until browned. Divide tomato sauce and sausage among halves and top with cheese. Broil until cheese is browned and squash warmed through, 4 to 5 minutes. Serve hot.