Preheat oven to 400 degrees and cut enough of the top of the head of garlic off so your cloves are exposed.
Take a large enough square of aluminum foil put your garlic in the center then generously drizzle olive oil in it and add some salt, create a tight seal so no oil leaks out and the garlic will roast perfectly inside.
Bake for 40 min, you know it is done when the cloves are slightly browned. With a knife see if you can squish the clove if so, at this point if you were to squeeze them the cloves should squirt out like toothpaste, don’t squeeze yet, just set to the side until your soup is done.
While the garlic is roasting, in a skillet cook bacon and set aside for later but reserve half of the bacon fat for the soup while keeping the other half for cooking the red onion.
Cook red onion in bacon fat until slightly caramelized add a little bit of salt then Marsala wine cook down until the onions have absorbed the marsala wine.
In your instant pot add butternut squash, cauliflower, broth, spices marsala red onions, and reserved bacon fat to your Instant Pot.
Make sure your seal is set to sealed and not in the vent position. Close the instant pot and cook on high pressure for 7 min. Keep in mind it will take a few mins to come to pressure then it will cook for 7 mins.
Do a quick release then add the roasted garlic cloves and remaining ingredients.
Use an immersion blender and blend until smooth, alternatively you can wait for it to cool before pureeing in a blender. Taste and adjust if needed. Garnish with your choice of toppings maybe some roasted pumpkin seeds, fresh rosemary, fresh thyme, and/or bacon you set aside earlier.