In a large pot, add cauliflower and potatoes. Cover with 2 cups of chicken stock and turn heat to medium-high.
Allow cauliflower and potatoes to cook for 25-30 minutes or until fork tender.
Using an immersion blender or regular blender, blend until small chunks or totally smooth, depending on preference. Set aside.
In a large soup pot or dutch oven, heat olive oil over medium-high heat. Add onion, carrots, and celery and saute 7-8 minutes or until veggies have softened.
Add in ground beef and garlic and saute until beef is no longer pink.
Throw in dill, salt, and pepper and stir until all combined.
Add the remaining chicken stock to the soup pot. Then pour in the pureed cauliflower and potato mixture. Turn heat down to medium.
Stir in the cheddar cheese and the pickle juice. Let soup simmer for 10-15 minutes, stirring occasionally.
Serve with more cheese, fresh dill, pickles, and bacon.