Cut tops off garlic. Place on large sheet of foil. Drizzle with olive oil and season liberally with salt and pepper. Bring sides together of foil to create a package. Place on a baking sheet and roast for 30-40 minutes. Cool and squeeze out roasted garlic.
Toss cauliflower and red pepper with 1 tablespoon olive oil and ¾ teaspoon salt.
Roast for 30 minutes and then turn the broiler on. Broil until cauliflower is slightly blackened, about 15 minutes. Remove from oven, but leave red pepper in until charred on all sides, another 5-10 minutes.
Peel skin off of red pepper.
Working in batches transfer roasted cauliflower, red pepper and roasted garlic to a blender, add in ½ cup chicken stock or more to help puree the soup. Blend until completely smooth.
Transfer to a stockpot. Add the rest of the chicken stock. Simmer for 10-15 minutes. Add ½ and ½ and season with plenty of salt and pepper.
While soup is simmering make croutons. Reduce the heat on the oven to 325 degrees. Toss bread with remaining olive oil, ⅛ teaspoon salt and garlic powder. Bake until golden brown, about 8 minutes.
Serve soup with croutons, drizzle of olive oil and grated parmesan cheese.
Recipe by Cooking for Keeps at https://www.cookingforkeeps.com/creamy-roasted-cauliflower-red-pepper-soup/