Preheat the oven to 425° F.
Line two baking sheets with parchment paper. Place the squash on one sheet and the Brussels sprouts on the other. Sprinkle both sheets with salt and pepper and 1 tablespoon of the olive oil.
Bake for 25 minutes, stirring the veggies halfway through. Once done, reduce the heat to 400° F.
Heat a large skillet over medium heat and add 2 tablespoons of the oil. Cook the onions until translucent, then add the garlic and cook about 30 seconds.
Stir in the chicken sausage and fresh herbs, and cook until the sausage is browned on the outside.
Add in the cauliflower rice, apples, almonds and cinnamon. Cook and stir until the cauliflower rice and apples begin to soften. Stir in the cranberries and season with salt and pepper to taste, then remove from heat.
Combine the rice/sausage mixture with the roasted squash/Brussels sprouts in a 9 x 13” baking dish (coated with cooking spray).
Bake in the oven (at 400° F) for 12-15 minutes or until the top is toasty. Serve garnished with fresh herbs if desired.