In a large stainless steel skillet over medium-high heat, heat 1 Tbsp. oil and swirl pan to coat. In a large bowl, toss steak with Italian seasoning; season with salt and pepper. Arrange steak in a single layer in skillet and cook, undisturbed, until underside is browned, about 2 minutes. Stir and continue to cook, stirring occasionally, until no longer pink, 1 to 2 minutes more. Transfer steak to a large bowl.

Reduce heat to medium. In the same skillet, cook mushrooms, stirring occasionally, until starting to brown, 8 to 10 minutes; season with a pinch of salt. Transfer to bowl with steak.

In the same skillet over medium heat, heat remaining 1 Tbsp. oil. Add onion and bell peppers; season with salt. Cook, stirring frequently, until peppers are softened, 8 to 10 minutes. Add garlic and cook, stirring, until fragrant, about 1 minute more. Transfer to bowl with mushrooms and steak.

Increase heat to medium-high. Pour in broth, scraping any browned bits from bottom of pan. Stir in half-and-half and bring to a simmer. Add pasta in a single layer and return to a simmer. Cover and cook, stirring occasionally, until pasta is al dente and sauce is thickened, 10 to 12 minutes.

Stir in provolone until melted. Return beef mixture to skillet and toss until coated.