Preheat your oven to 400°F (200°C). Toss the cubed butternut squash with 1 tablespoon of olive oil, salt, and pepper. Spread evenly on a baking sheet and roast for 25-30 minutes, or until tender and slightly caramelized. Set aside.
In a large pan or Dutch oven, heat the remaining 1 tablespoon of olive oil over medium heat. Add the chopped onion and cook for 4-5 minutes, until softened. Add the minced garlic and cook for another minute until fragrant.
Add the Arborio rice to the pan and stir to coat the grains in the oil. Toast for 2-3 minutes until the edges of the rice become translucent. Add 1 teaspoon of Italian seasoning and stir to combine, allowing the herbs to bloom.
Pour in the white wine (if using), stirring until it’s mostly absorbed by the rice.
Begin adding the warm vegetable broth, one ladleful at a time, stirring frequently. Wait for each ladle of broth to be absorbed before adding more. Continue this process for 18-20 minutes, or until the rice is creamy and tender but still has a slight bite. You may not need all the broth.
Stir in the roasted butternut squash and sliced sage leaves. Cook for another 2-3 minutes to combine the flavors.
Remove the risotto from the heat and stir in the butter and Parmesan cheese. Season with salt and freshly cracked pepper to taste.
Serve hot, garnished with extra fresh sage leaves and a sprinkle of Parmesan or nutritional yeast.