Preheat the oven to 425 degrees.
Add the cauliflower to a parchment lined baking sheet.
Drizzle with olive oil, and sprinkle with salt and pepper to taste.
Roast the cauliflower for 20 minutes.
While the cauliflower is roasting, add the butter to a skillet or pot over medium heat.
Saute the garlic in the melted butter for one minute.
Pour in the heavy whipping cream and pumpkin puree, and whisk to combine.
Season with salt and pepper to taste.
Mix in the paprika, shredded cheddar, bacon and parmesan cheese.
Stir until the cheese has melted.
Add additional heavy whipping cream or chicken broth if the mixture is too thick.
Stir the roasted cauliflower into the cheese sauce, and toss to combine well.
Serve garnished with additional bacon.