Roast the squash: Place a rack in the center of your oven and preheat to 400°F. Line a large rimmed baking sheet with parchment paper. Place the squash in the center of the pan, drizzle with the oil, and sprinkle with 1/4 teaspoon salt and 1/4 teaspoon pepper. Spread into a single layer on the prepared baking sheet. Roast in the oven until the squash is tender, turning once halfway through, about 20 minutes. Set aside.

Meanwhile, in a saucepan, warm the chicken stock. Keep a ladle handy for adding the warm liquid to the risotto. It should be fairly warm and steaming, but not boiling.

In a Dutch oven or similar sturdy pot, melt the butter over medium low. Add the bacon and shallot. Sauté for 5 minutes.

Add the rice and garlic, stirring to coat the grains with the cooking oils. Stir in the wine and let simmer for 1 minute.

Carefully add 2 big ladles of the chicken stock to the rice. Add the remaining 1/2 teaspoon salt salt and 1/4 teaspoon pepper. Let the risotto simmer over low heat until the liquid is almost completely absorbed, stirring every few minutes to help the rice cook evenly and ensure nothing sticks to the bottom. This will take 5 or so. You don’t have to stir risotto constantly. Just, check in on it periodically and stir.

As soon as most of the liquid has been absorbed and the rice is about to look dry, add 2 more ladelfuls of stock. Stir as before, until most of the new liquid is absorbed. Repeat, adding the stock 2 ladelfuls at a time, until the risotto is creamy and the rice tender but still a little bit al dente, about 15 to 30 minutes total. If you run out of stock, simply use water until the risotto reaches your desired consistency and texture.

Stir in the Parmesan, sage, and roasted butternut squash. Let cook a few minutes to warm through. Taste and adjust seasoning as desired. Serve hot, with more Parm sprinkled on top.