Prep the chicken: Slice each chicken breast into thinner cutlets by carefully cutting horizontally. You should end up with even pieces about 1/4 inch thick.
Season the chicken: Generously sprinkle both sides with Italian seasoning, paprika, kosher salt, and pepper.
Lightly flour: Dredge each cutlet in flour, shaking off any excess.
Sauté the asparagus: Heat 2 tablespoons olive oil in a large skillet over medium-high. Add asparagus, season with salt and pepper, and cook for 3 to 5 minutes, tossing occasionally. Transfer to a plate.
Cook the chicken: Add a drizzle of olive oil to the skillet. Sear chicken until golden on both sides, about 3 minutes per side.
Make the sauce: Add garlic to the skillet, stirring for 30 seconds. Pour in wine, reducing by half, then add lemon juice and chicken broth.
Simmer and finish: Reduce the heat to low, cover, and cook chicken in the sauce for about 7 to 8 minutes until it reaches 165°F. Add asparagus back to the skillet in the final two minutes to reheat. Serve immediately.