Preheat oven to 350 degrees and line a baking sheet with parchment paper.
Rinse cauliflower and pat dry with paper towels.
Rough chop cauliflower into 1" chunks.
Roast at 350 until lightly browned, about 15 minutes.
Cook the bacon in a large dutch oven or stock pot over medium high heat until crisp.
Remove the bacon from the pot and set aside.
Add the Italian sausage to the bacon drippings and cook until brown (approximately 5 minutes).
Set the sausage aside. Keep the sausage and bacon drippings in the pot as this flavors the soup.
Lower the heat to medium low.
Add the diced red onion, minced garlic, and the roasted cauliflower florets to the pot. Cook for 2-3 minutes, until soft and fragrant.
Increase the heat to high and pour in the chicken broth, coconut aminos, vinegar, red pepper flakes, salt, and pepper.
Stir to combine and add the bacon and sausage back to the pot.
Bring to a boil.
Once boiling add the kale and lower the heat to a simmer. Cook for 5 minutes.
Remove from heat and stir in the heavy whipping cream.
Return to heat and cook for 3 more minutes.
Serve immediately and enjoy!