Preheat oven to 370 degrees F.
Line a baking sheet with parchment paper and set aside.
Pour olive oil over the acorn squash and sprinkle with paprika, salt and pepper.
Bake in over for 50-60 minutes, until skin is soft and fork-tender.
While squash is cooking, heat 1 tablespoon olive oil in a skillet over medium-high heat.
Add sausage and using a wood spoon break into coarse pieces. Cook until brown. It’s about 5-6 minutes. Then, set it aside.
In the same skillet, add remaining 1 tablespoon oil and onions; cook until they’re soft, 3 minutes. Add garlic and cook for 30 seconds.
Add mushroom and cook for 3 to 5 minutes. Stir occasionally.
Add kale and toss; add tomato sauce and cover the skillet with a lid and cook until kale is tender.
Bring back the sausage and stir well to combine.
Divide kale-sausage filling among squash.
Top with Parmesan if you desire before serving. Enjoy!