Preheat your oven to 400°F.
Rub the squash halves with olive oil and sprinkle with salt and pepper. Place the 4 squash halves cut-side down on a parchment-lined baking sheet and roast for 20 - 30 minutes, or until the top of the squash feels tender when gently pressed.
While waiting for the squash to roast, start your filling. Start with caramelizing the onions. In a medium skillet (I use a cast iron), melt 3 Tbsp of the coconut oil over med-low heat and add all the onions, stirring to coat. Sprinkle with salt and continue to cook, stirring every 5 minutes or so to prevent burning. The onions will take at least 25 minutes to become caramelized. Make sure they are truly caramelized and not simply sauteéd. They will become a deep golden brown color and reduce down by about three-fourths. If after a while, you would like to speed things along, you can sprinkle them with a little organic sugar so they caramelize faster. Remove from heat and set aside.
While the squash roasts and the onions cook, melt the remaining 2 teaspoons of coconut oil in a large skillet over med-low heat. Add the garlic and stir until browned.
Carefully peel back the casings from the sausages and crumble the sausage into the skillet with the garlic. Add the apples, kale, and herbs and continue to cook, stirring occasionally, until the apples soften and the sausage has browned. Add salt and pepper to taste.
Stir the caramelized onions into the sausage mixture. Next, fill all 4 halves of the squash with the onion and sausage mixture.
Preheat the broiler.
Place the squash halves on the baking sheet, stuffing side up. Once the broiler is preheated, put the squash under the broiler for 5 - 10 minutes or until the tops have browned (but frequently check to make sure they haven't burned). Allow to cool briefly and serve warm. Enjoy!