Preheat your oven to 400°F and line a large baking sheet with parchment paper or aluminum foil for easy cleanup.

Cut each acorn squash in half lengthwise from stem to blossom end, then use a sturdy spoon to scoop out all seeds and stringy pulp from the cavity.

Brush the cut surface of each squash half with olive oil (about 1 tablespoon total) and season generously with salt and black pepper.

Place squash halves cut-side down on the prepared baking sheet and roast for 25-30 minutes until the flesh is tender when pierced with a fork and starting to caramelize.

While the squash roasts, heat remaining olive oil in a large skillet over medium-high heat and add the Italian sausage, breaking it up with a wooden spoon.

Cook the sausage for 5-7 minutes until browned and cooked through with crispy edges, then add diced onion and minced garlic to the skillet.

Sauté the aromatics for 3-4 minutes until softened and fragrant, then stir in dried sage, thyme, oregano, salt, and pepper.

Add uncooked rice to the skillet along with chicken or vegetable broth, bring to a boil, then reduce heat to low and cover.

Simmer for 15-18 minutes until rice is tender and has absorbed most of the liquid, then remove from heat and let stand covered.

Remove roasted squash from oven and carefully flip each half cut-side up, creating cavities ready for filling.

Divide the sausage and rice mixture evenly among the four squash halves, mounding it generously in each cavity.

Return filled squash to the oven and bake for an additional 20-25 minutes until filling is hot throughout and top begins to brown.

Remove from oven and immediately sprinkle each squash half with grated parmesan cheese, then return to oven for 3-5 minutes.

Once cheese is melted and golden, remove from oven and garnish generously with chopped fresh parsley or sage leaves.

Serve hot, optionally drizzled with additional olive oil and sprinkled with red pepper flakes for those who enjoy extra heat.