Prep the peppers: Heat oven to 375°F (190°C). Slice the tops off the bell peppers and remove seeds and membranes.
If they wobble, shave a thin slice off the bottom to help them stand.
Pre-bake for tenderness: Place peppers cut-side up in a baking dish. Drizzle with olive oil and a pinch of salt. Add 1/4 cup water or broth to the dish.
Cover with foil and bake for 12–15 minutes to soften slightly.
Crisp the bacon: In a large skillet over medium heat, cook chopped bacon until crisp. Use a slotted spoon to transfer bacon to a plate. Leave 1–2 tablespoons of bacon fat in the pan.
Sauté aromatics: Add the onion to the skillet.
Cook 3–4 minutes until softened. Stir in garlic and cook 30 seconds until fragrant.
Brown the beef: Add ground beef, breaking it up with a spoon. Season with salt, pepper, smoked paprika, and chili powder if using.
Cook until browned and no longer pink, about 5–7 minutes. Drain excess fat if needed.
Build the burger flavor: Stir in BBQ sauce, ketchup, mustard, and Worcestershire. Simmer 2–3 minutes until glossy and slightly thickened.
Taste and adjust seasoning.
Add the mix-ins: Remove from heat. Fold in half the cheddar, the crisp bacon, and chopped pickles. This gives you gooey pockets of cheese and that signature burger tang.
Stuff the peppers: Remove peppers from the oven.
Spoon the beef mixture into each pepper, packing it in. Top with the remaining cheddar.
Bake to finish: Return peppers to the oven (uncovered) for 10–15 minutes, until the cheese is melted and bubbly and peppers are tender.
Garnish and serve: Drizzle a little extra BBQ sauce on top, sprinkle with green onions and extra pickles, and serve hot.