Preheat oven to 350F. Place the squash on a parchment-covered baking sheet and bake it for 15-20 minutes (until just tender). Set aside.
In a large wok-pan, eat EVOO and brown the sausage, adding fennel at the end. Set aside.
Add the onion to the pan until lightly caramelized. Add half the garlic. Combine the pork into the pan and set aside.
Rice the cauliflower with grater. Spread it out on paper towels.
Pan-fry the prosciutto on a large surface area non-stick pan. Set aside on paper towels. In the same pan, lightly brown the cauliflower in hot EVOO, adding in butter and the other half of the garlic as you go.
Chop and combine the fresh herbs together.
Re-heat the sausage and onion mixture to medium high. Add the broth and boil down. Add the cauliflower, the squash, and the herbs. Mix well and heat for 5 minutes.
Place the mixture into a 13x9 baking dish. Bake at 400F for 30 minutes. Top with cheese and cut-up prosciutto, and continue baking for 5 minutes. Cool before serving.