Bring a large pot of salted water to a boil and cook the tortellini according to the package instructions, typically about 3-5 minutes for fresh tortellini. Once cooked, drain and set aside.
Cook the Steak:
In a large skillet, heat 1 tablespoon of olive oil over medium-high heat. Add the thinly sliced beef and cook, stirring frequently, until browned and cooked through, about 5-7 minutes. Season with a pinch of salt and pepper.
Once the beef is cooked, remove it from the skillet and set aside.
Sauté the Vegetables:
In the same skillet, add a little more olive oil if needed. Add the sliced onion and bell pepper, and cook over medium heat until softened and slightly caramelized, about 5-7 minutes.
Add the minced garlic and cook for another 1-2 minutes, until fragrant.
Make the Sauce:
Pour in the beef broth and Worcestershire sauce, stirring to combine. Let it simmer for a couple of minutes to reduce slightly.
Reduce the heat to low and add the heavy cream, stirring until the sauce becomes smooth and creamy.
Combine Everything:
Add the cooked beef back into the skillet, along with the drained tortellini. Stir everything together until the tortellini is coated with the creamy sauce and the beef and vegetables are evenly distributed.
Add the Cheese:
Sprinkle in the shredded provolone cheese and stir until it melts into the sauce and creates a creamy, cheesy coating. Taste and adjust seasoning with more salt and pepper if needed.
Serve:
Transfer the Philly Cheesesteak Tortellini Pasta to serving plates. Garnish with freshly chopped parsley, if desired.