Brown the beef: Heat oil in a large skillet over medium-high. Add ground beef and onion.
Cook until beef is no longer pink and onions are soft, about 6–8 minutes. Stir in garlic for the last minute. Drain excess fat.
Season the mixture: Stir in salt, pepper, smoked paprika, mustard, and Worcestershire.
Fold in drained diced tomatoes and chopped pickles. Taste and adjust seasoning.
Prep the creamy base: In a bowl, whisk together softened cream cheese and heavy cream until smooth. If needed, microwave for 10–15 seconds to help it blend.
Stir in 1 cup shredded cheddar.
Layer in the crockpot: Lightly grease the slow cooker. Add cauliflower rice to the bottom and spread evenly. Top with the beef mixture.
Pour the cream cheese mixture over the top and spread. Sprinkle with 1 cup cheddar.
Cook low and slow: Cover and cook on Low for 3–4 hours or on High for 1.5–2 hours, until hot and bubbly and the cauliflower is tender.
Finish with cheese: During the last 15 minutes, add the remaining 1 cup cheddar on top. Cover to melt.
Garnish and serve: Let rest 10 minutes to set.
Top with sliced green onions, extra pickles, shredded lettuce, or a drizzle of sugar-free ketchup or hot sauce. Scoop and enjoy.