Prep the peppers. Preheat your oven to 375°F (190°C).
Slice the tops off the bell peppers and remove seeds and membranes. If they don’t stand upright, trim a thin slice off the bottom so they sit flat. Place in a baking dish, open side up.
Par-bake (optional but recommended). Brush or spray the peppers lightly with oil and bake for 10 minutes to soften.
This helps them cook evenly and shortens total time.
Sauté aromatics. Heat oil in a large skillet over medium heat. Add the onion with a pinch of salt and cook 3–4 minutes until softened. Stir in the garlic and cook 30 seconds until fragrant.
Brown the beef. Add ground beef to the skillet.
Cook, breaking it up, until no pink remains, about 5–7 minutes. If there’s excess grease, drain it.
Season and build flavor. Stir in tomato paste, mustard, Worcestershire, smoked paprika, 1/2 teaspoon salt, and a few grinds of pepper. Cook 2 minutes to let the tomato paste caramelize slightly.
Add cheeseburger touches. Stir in low-sugar ketchup and chopped pickles.
Taste and adjust seasoning. Turn off heat and fold in 1 cup of shredded cheddar until just melted.
Stuff the peppers. Spoon the beef mixture into each pepper, mounding slightly. Top each with remaining cheddar.
Bake. Return the dish to the oven and bake 15–18 minutes, until the peppers are tender and the cheese is melted and bubbly.
Finish and serve. Let cool for 5 minutes.
Garnish with shredded lettuce, diced tomatoes, and extra pickles if you like. Serve warm.