Preheat oven to 400F, line a large baking sheet with parchment paper or a piece of foil.
Remove any leaves from the cauliflower, chop into large florets.
Peel and slice onion, peel garlic..
Arrange cauliflower florets, onion, and garlic in a single layer on the prepared baking sheet, drizzle generously with olive oil, sprinkle with salt and pepper.
Let veggies roast for about 50 minutes, stirring every 15-20 minutes or so until golden brown
Transfer roasted veggies and garlic to a large pot or dutch oven.
Add chicken broth, milk, and white wine to the soup pot, mash lightly with a potato masher.
Bring almost to a boil over medium-high heat, turn heat down and simmer for 20 minutes.
Puree soup mixture until smooth – you may need to do this in batches, depending on the size of your food processor or regular blender. Alternately, you can use an immersion blender, right in the pot.
Transfer smooth puree back to the pot, add heavy cream and stir well. Season with salt and pepper, to taste.
Stir smoked serrano powder into oil, drizzle over individual servings of soup.