Prep the peppers. Preheat your oven to 375°F (190°C).
Slice the tops off the bell peppers and remove seeds and membranes. If needed, trim the bottoms slightly so they stand up in the baking dish.
Soften the peppers. Place peppers upright in a baking dish. Drizzle with a little olive oil and a pinch of salt.
Bake for 10–12 minutes to start softening while you make the filling.
Cook the aromatics. Heat a large skillet over medium heat. Add olive oil, then the onion with a pinch of salt. Cook 3–4 minutes until softened.
Stir in garlic and cook 30 seconds until fragrant.
Brown the beef. Add ground beef to the skillet. Break it up and cook until no longer pink, 6–8 minutes. If there’s excess grease, drain most of it, leaving 1–2 teaspoons for flavor.
Season and sauce. Stir in smoked paprika, onion powder, garlic powder, salt, and pepper.
Add sugar-free ketchup, mustard, and Worcestershire. Cook 2 minutes, letting everything meld.
Make it cheesy. Reduce heat to low. Stir in cream cheese until melted and creamy.
Add mayonnaise for extra richness. Fold in chopped pickles and 1 cup shredded cheddar. The mixture should be thick and scoopable.
Fill the peppers. Remove peppers from the oven.
Spoon the beef mixture evenly into each pepper, packing it in gently.
Top and bake. Sprinkle the remaining 1/2 cup cheddar over the peppers. Return to the oven and bake 12–15 minutes, until the cheese is melted and bubbly and the peppers are tender.
Finish and serve. Top with extra pickles, crumbled bacon, or jalapeños if you like. Let them rest 5 minutes, then serve hot.
For a “burger plate” feel, add shredded lettuce on the side and a drizzle of sugar-free ketchup or a simple burger sauce.