Prep the peppers: Preheat your oven to 400°F (200°C). Slice the tops off the bell peppers and remove seeds and membranes. If they wobble, trim a thin slice off the bottom to level.
Soften the shells: Place peppers in a baking dish, drizzle with a little oil and a pinch of salt, and bake for 10–12 minutes.
You want them slightly tender but still sturdy.
Sauté onions and mushrooms: Heat 1 tablespoon oil in a large skillet over medium-high heat. Add onions and a pinch of salt; cook 5–7 minutes until softened and caramelized at the edges. Add mushrooms and butter; cook another 4–5 minutes until browned.
Stir in garlic for the last 30 seconds. Transfer to a bowl.
Cook the steak: In the same skillet, add another tablespoon of oil. Increase heat to high.
Season steak with salt, pepper, and optional garlic/onion powder. Sear in batches for 1–3 minutes total, just until browned but still tender. Don’t overcook.
Combine and season: Add the onion-mushroom mixture back to the skillet with the steak.
Stir in Worcestershire if using. Taste and adjust seasoning. Remove from heat.
Cheese layer #1: Place a slice of Provolone (or a sprinkle of mozzarella) inside each pepper to form a cheesy base.
Fill the peppers: Spoon the steak mixture into each pepper, packing it gently.
If using Cheez Whiz, drizzle 1–2 teaspoons over the filling for that signature Philly vibe.
Cheese layer #2: Top each pepper with another slice of Provolone or a generous sprinkle of shredded cheese.
Bake until melty: Return the stuffed peppers to the oven for 8–10 minutes, or until the cheese melts and the peppers are tender to your liking.
Finish and serve: Let rest 3 minutes. Garnish with cracked black pepper. Serve hot with a crisp side salad or roasted broccoli.