Preheat the oven to 400 degrees Fahrenheit.
Rinse both acorn squash and microwave for 1 minute. Using a sharp knife, slice them in half and place in a baking dish with 1 inch water. Drizzle with olive oil, salt, pepper, and bake for 30 minutes. Flip the halves and continue to cook for 30 minutes.
While the acorn squash is cooking, begin cooking to rice according to the directions on the bag.
While the rice and acorn squash are both cooking, begin cooking the stuffing. In a large skillet over medium heat, begin heating the olive oil and cook down the onions and celery.
Add in the sausage- using a wooden spoon break down into smaller pieces. Add the rosemary and paprika, cover with a lid and continue to cook.
When the sausage is done cooking, reduce the heat and add the pecans and cranberries. Cover with a lid and continue to cook for 5-10 minutes or until the cranberries begin to soften.
Serve with the rice on the bottom, acorn squash on top stuffed with the sausage mixture.