In a large pot over medium-high heat, melt 1 tablespoon grass-fed butter and then add in the 5 garlic cloves, stirring constantly for about 1 minute.
Add in the 1½ cups chicken bone broth and 1 cup water and bring to a boil.
Cut up the 1 head of cauliflower into small florets and add it to the pot.
Add the 1 teaspoon ground black pepper, ½ teaspoon Old Bay Seasoning, ½ teaspoon dried oregano, and ½ teaspoon kosher salt and simmer over medium heat for about 15 minutes.
Once the cauliflower is tender, remove from heat and use an immersion blender to blend up about half of the florets in the pot. You want the mixture to be chunky yet start to look creamy.
Add the pot back to the heat and add in the 8 ounces cream cheese, 4 slices bacon + drippings (chopped). Stir frequently until the cream cheese has fully melted.
Ladle into bowls and top with additional crumbles bacon and a drizzle of olive oil. Store any leftovers in the fridge in an air-tight container.