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Heat olive oil in a large skillet over medium-high heat. Season steaks generously with salt, black pepper, and cayenne. Cook steaks in hot oil for 5 to 6 minutes. Flip and add onions around steaks. Continue cooking until steaks begin to firm and are hot and slightly pink in the center, 5 to 6 minutes more. Push onions under steaks and cook until browned but still crunchy, 2 to 3 minutes more. Remove steaks and sautéed onions to a plate.
Preheat the oven to 425 degrees F (220 degrees C). Line a baking tray with aluminum foil.
Place rolls on the prepared baking tray. Hollow out the top of each roll by cutting in at a 45-degree angle. Pinch off some of the bread inside to make room for the filling.
Slice steaks into thin strips, then across into ½-inch pieces. Transfer to a mixing bowl. Add sautéed onions and accumulated meat juices. Toss in 1 ½ cups provolone, pickled peppers, cream cheese, 1 teaspoon kosher salt, and ¼ teaspoon black pepper; mix until thoroughly combined. Taste and season with salt if needed. Spoon filling into rolls and top with remaining 1 cup provolone cheese.
Bake in the preheated oven until cheese is melted and the edges of rolls start to brown, about 15 minutes.