Preheat your oven to 425°F and line a baking sheet with foil, lightly misting it with cooking spray.
In a large bowl, combine the cubed butternut squash and diced Honeycrisp apples.
Drizzle about 2 tablespoons of olive oil over the mixture, then sprinkle generously with salt and black pepper.
Add 1 tablespoon pure maple syrup, dried ground sage, and herbes de Provence.
Toss everything together to evenly coat.
Spread the mixture out on the prepared baking sheet and roast for about 35 minutes, stirring occasionally for even roasting, until the squash is tender.
While the squash and apples are roasting, heat a large skillet (cast-iron works great) over medium-high heat.
Add a small drizzle of olive oil.
Once the pan is hot, add the crumbled sweet Italian sausage.
Cook for a few minutes, stirring occasionally, until the sausage is browned and cooked through.
Remove the sausage from the skillet and set aside in a bowl.
If the skillet looks a bit dry, add a touch more olive oil.
Add the sliced fennel and onion to the pan and cook over medium heat, caramelizing together for about 10-12 minutes.
Stir occasionally until the vegetables are deeply golden and jammy in texture.
Remove from the pan and add to the bowl with the cooked sausage.
Switch your oven setting to broil.
In a large bowl, combine the roasted butternut squash/apples (from Step 1) with the sausage, fennel, and onion mixture (from Steps 2 and 3).
Pour in the remaining 1 tablespoon maple syrup and toss everything together to blend flavors.
Season with salt and pepper to taste, creating a sweet-savory balance.
Transfer the mixture to a medium baking dish, about 9 by 13 inches.
If you’d like a crispy sage garnish, heat ¼ cup oil in a small saucepan over medium-high heat.
Once shimmering, add the sage leaves and fry for about 20 seconds until crisp.
Immediately remove the leaves to a paper towel to drain, and sprinkle lightly with salt.
Top the assembled casserole (from Step 4) with the shredded Gruyere cheese.
Place the baking dish under the broiler for a few minutes, just until the cheese is melted and golden-brown.
Keep a close eye, as broilers can brown things quickly!
Remove the casserole from the oven and let cool slightly.
Garnish with either fried sage leaves (from Step 5) or fresh sage leaves.
Serve warm and enjoy the blend of sweet, savory, and herbal flavors.
