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Preheat the oven to 425°F. Spray with cooking spray or grease a deep 9x13-inch baking dish.
In the baking dish, combine the butternut squash, olive oil, ½ teaspoon of the salt, garlic and Italian seasoning, tossing to coat. Add the chicken sausage (crumbled or broken into pieces) evenly over the butternut squash.
Roast for 20–25 minutes, uncovered, stirring once, until the squash is tender and the sausage is cooked through.
Remove the pan from the oven. Stir in the dry orzo, ½ teaspoon of salt, and chicken broth. Nestle the whole Boursin cheese into the center. Sprinkle with red pepper flakes if you’d like a little kick.
Return to the oven and bake, uncovered, for 20–25 minutes, stirring once halfway through, until the orzo is tender and the liquid is mostly absorbed. Let it sit for 5 minutes, then stir everything together until creamy. Finish with fresh parsley if you like.