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Preheat the oven to 450 degrees F and line a sheet tray with foil.
Peel and clean the squash and cut into one-inch pieces and lay out on the sheet tray with the olive oil and black pepper. Roast for ten minutes, flip and roast for ten more. Remove and set aside.
Bring a large saucepan of water to a boil with some salt. Once boiling, add the pasta and cook per box directions. Drain and rinse with cold water and set aside.
Spray the bottom of a medium soup pot with kitchen pan spray and bring heat to medium high. Once hot, add the sausage meat and break it up and brown using a wooden spoon, about five minutes.
Once browned, move the cooked sausage to the pan edges and add the butter. Once melted, add leeks, carrots, and celery, and cook for three minutes.
Add garlic, thyme, sage, and red pepper flakes and cook for two minutes.
Add hot stock and bring to a simmer and simmer until the vegetables are tender, about 15 minutes.
Add the spinach, cooked squash, Parmesan cheese and heavy cream and heat to serving temperature.
Use a ladle and skim off any fat floating on top, then taste the soup for salt and salt only if needed.
Place cooked pasta into serving bowls and pour hot soup over. Top with grated Parmesan cheese and serve.