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Preheat oven to 400°F.
Roast your butternut squash until soft, about 25 minutes at 400°F.
Grate all of your cheeses and set aside.
When the squash is out of the oven, let it cool slightly and scoop out the soft inside, removing it from the skin. Then add to a blender. Add the milk, garlic powder, rosemary, thyme, sage, paprika, nutmeg and cayenne. Blend until smooth.
Put a large pot or dutch oven on medium heat. Add in the olive oil and bay leaf. Stir in the butternut purée and begin to cook down.
Keep this sauce on low heat while you cook your pasta in a separate pot, stir occasionally.
Cook the pasta in boiling water until al dente, about 6-8 minutes, drain and reserve about ½ cup of the pasta water.
Pour the pasta into the sauce. Alternate between adding the cheeses and a splash of pasta water. Stir until the sauce fully coats the pasta and the cheese is melted.
Top with red pepper flakes and a drizzle of chili oil if you'd like some heat, and serve warm.