In a large pot, heat 1 tablespoon of olive oil over medium heat. Add the mild Italian sausage, cooking until browned and crispy, about 8-10 minutes. Remove the meats from the pot, leaving about 2 tablespoons of grease.

In the same pot, add another tablespoon of olive oil if needed, and toss in the chopped onions. Sauté for 3-4 minutes until they soften. Add minced garlic and cook for an additional 1-2 minutes until fragrant.

Add the cauliflower florets to the pot along with the chicken broth. Season with salt and pepper. Bring to a gentle boil, then let it simmer uncovered for about 15 minutes until the cauliflower is tender.

Once tender, remove the pot from heat. Using an immersion blender, blend until smooth. If using a regular blender, let it cool slightly before blending in batches.

Return the blended soup to low heat. Stir in the half and half, cooked sausage, and crispy bacon. Add the curly kale and let it simmer for another 5 minutes until the kale wilts.