Heat a large pot over medium heat and add the bacon. Cook the bacon until crispy, remove it to a paper towel-lined plate to cool, then chop the bacon into small pieces and set aside.
Drain the bacon fat out of the pot, then add the Italian sausage (casings removed) and cook until browned, breaking it up into small pieces as it cooks. Remove the sausage to a paper towel-lined plate and set aside.
Drain the fat from the pot again and add the diced onion, diced red pepper, and garlic, along with the salt, pepper and red pepper flakes.
Saute over medium heat until the onion and pepper are soft.
Add the white wine and deglaze the pan, scraping up all the brown bits in the bottom of the pan.
Once the wine evaporates, add the chicken broth and the cauliflower.
Cover the pot and let the cauliflower cook in the broth until fork tender (this should take less than 10 minutes).
Once the cauliflower is cooked through, turn off the heat under the pot.
Add the sausage back into the pot, along with the heavy cream, parmesan and kale, and stir well. The kale will wilt in a minute or two, and the parmesan will melt into the creamy soup.
Top the soup with the crispy bacon, and some additional grated parmesan when serving.