Prepare the Peppers: Slice the bell peppers in half lengthwise and carefully remove the seeds and white membranes. Arrange the pepper halves cut-side up in a lightly greased baking dish. If you prefer softer peppers, you can pre-bake them for about 8 to 10 minutes before adding the filling. Personally, I love this extra step because it helps create more tender roasted peppers while preventing excess moisture later.
Cook the Steak Filling: Heat olive oil in a large skillet over medium-high heat. Add the sliced onions and mushrooms, then sauté until softened, golden, and slightly caramelized. Stir occasionally to develop deeper savory flavor. Add the minced garlic and cook briefly until fragrant before adding the thinly sliced steak to the skillet.
Add Seasoning: Season the steak mixture with Worcestershire sauce, salt, black pepper, and Italian seasoning. Continue cooking until the steak is browned but still juicy and tender. Be careful not to overcook the meat since it will continue cooking in the oven later. The onions, mushrooms, garlic, and steak together honestly create the classic cheesesteak aroma that makes this recipe so comforting.
Stuff the Peppers: Spoon the hot steak filling generously into each prepared bell pepper half. Press the filling down lightly so every pepper holds plenty of savory steak, onions, mushrooms, and flavorful juices.
Add Cheese: Top each stuffed pepper with provolone cheese slices, making sure the filling is fully covered. As the peppers bake, the cheese melts into the steak mixture and creates that rich creamy cheesesteak texture everyone loves.
Bake Until Tender: Place the baking dish into the oven and bake until the peppers become tender and the cheese turns bubbly and lightly golden on top. The roasted peppers soften beautifully while the cheesy steak filling stays juicy and packed with savory flavor.
Garnish and Serve: Remove the Cheese Steak Stuffed Peppers from the oven and let them rest for a few minutes before serving. Garnish with fresh parsley for a pop of freshness and color, then serve hot while the cheese is still perfectly melted and gooey.