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Preheat oven to 400°F.
On a rimmed baking dish, combine squash, 2 tablespoons olive oil, and ¼ teaspoon nutmeg. Season with salt and pepper.
Bake in preheated oven 20 minutes, stirring halfway through, until squash is fork tender but not mushy. Tent with foil to keep warm.
On another rimmed baking sheet, evenly spread out the prosciutto strips. Bake in preheated oven with the squash until crisp, about 15 minutes. Tent with foil to keep warm.
As squash and prosciutto bake, bring broth to a low simmer in a medium saucepan.
Heat remaining tablespoon of olive oil in a 5-quart, high-rimmed saucepan or heavy large pot over medium-high heat.
Add shallots and sauté until tender, about 3 minutes, stirring frequently. Stir in garlic and cook 1 minute.
Add rice and continually stir 1 minute. Stir in wine. Scrape any brownings off bottom of pan, and cook 2-3 minutes until wine is absorbed, stirring occasionally.
Add ¾ cup of warm broth and simmer until most of the broth is absorbed, stirring often, about 2 minutes.
Continue to add ¾ cup of broth at a time, allowing most of it to be absorbed after each addition, stirring often, about 20 minutes in total. Rice will become tender and creamy.
Lower heat to medium-low, stir in squash, prosciutto, sage and thyme into rice. Cook 2 minutes to combine flavors.
Remove from heat, stir in remaining ¼ teaspoon nutmeg and parmesan cheese. Season with salt and pepper. Serve hot. Enjoy!