Cut two acorn squash in half and scoop out seeds. Place them face down on a lined baking sheet. Bake for 45-60 minutes, or until fork tender.
While the acorn squash bakes, break apart and cook sausage in a heated cast iron skillet. When fully cooked through, remove from the skillet and set aside.
Remove the kale stems and add the kale to the skillet and cook in the remaining fat from the sausage. When fully cooked down, remove from skillet and set aside.
When the acorn squash finishes baking, scoop out the insides and add to a food processor. Add the cinnamon, onion powder, salt, fennel, and 1 Tbsp of fresh sage. Process until well combined and the squash is a smooth texture.
Combine the smooth squash mixture, kale, and sausage in a 9×13 baking dish.