Place an oven rack in the center position. Set a 12-inch cast-iron skillet inside the oven and preheat to 400°F (204°C). Preheating the skillet ensures the bacon becomes crisp as soon as it touches the surface.

Using a sharp knife, slice each chicken breast horizontally to create four evenly sized cutlets. Season both sides with salt and black pepper as needed. Sprinkle Cajun seasoning evenly across the cutlets to ensure uniform flavor distribution.

Wrap each cutlet with two slices of bacon, ensuring the bacon covers the surface as fully as possible. Overlapping is acceptable. Once wrapped, place the prepared cutlets on a plate or cutting board until ready to cook.

Carefully remove the hot skillet from the oven. Using tongs, place each bacon-wrapped cutlet seam-side down in the skillet. Return the skillet to the oven and bake for approximately 4 minutes, or until the bacon is crisp on the bottom.

Using tongs, flip each cutlet gently. Bake an additional 5–6 minutes, or until the bacon is fully crisp and the chicken is cooked through. If using larger chicken breasts, extend the cooking time by 5–10 minutes as needed to reach doneness.