
Philly Cheesesteak Stuffed Peppers star sirloin stuffed into peppers for a fun all-in-one meal inspired by Philly cheesesteak.
Heat oven to 375°F. On rimmed baking sheet, arrange pepper halves, cut sides down; drizzle with 1 tablespoon oil and season with 1/4 teaspoon each salt and pepper. Roast until peppers are slightly tender, 16 to 20 minutes. Transfer peppers, cut sides up, to 9- by 13-inch broil-safe baking dish. Arrange rack 4 to 6 inches from broiler and heat broiler to high.
Meanwhile, heat 1 tablespoon oil in large skillet on medium-high. Season steak with 1/4 teaspoon each salt and pepper, and cook in 2 batches until browned, 1 minute per side; transfer to bowl.
Heat 1 tablespoon oil in large skillet on medium. Add mushrooms and cook, undisturbed, 3 minutes. Season with 1/4 teaspoon salt and cook, tossing twice, until browned, 4 to 6 minutes; transfer to same bowl.
Add remaining tablespoon oil to skillet, then onion, and season with 1/4 teaspoon each salt and pepper; cook, covered, stirring occasionally (and lowering heat as necessary), until tender and starting to release liquid, 6 to 8 minutes. Reduce heat to medium-low and cook, uncovered, stirring occasionally, until caramelized (adding a splash of water if onions stick to pan or are browning too quickly), 10 to 12 minutes. Stir in red wine vinegar, scraping up any browned bits.
Add steak, mushrooms, and any juices to skillet and cook, tossing occasionally, to heat through, about 3 minutes.
Meanwhile, in small bowl, whisk together Worcestershire, Dijon, and 1 tablespoon water. Stir into skillet and cook 1 minute. Remove from heat and fold in cherry peppers and half of parsley. Divide mixture among cooked peppers and top with provolone. Broil until cheese is melted and golden brown, 2 to 3 minutes. Serve sprinkled with remaining parsley.