Let chicken breasts sit at room temperature for 15 minutes, then pat completely dry with paper towels.
Pound thicker ends to 1-inch thickness, then trim excess fat or connective tissue.
Mix garlic powder, paprika, onion powder, black pepper, salt, and cayenne in a small bowl.
Brush each breast with olive oil, then sprinkle seasoning generously on both sides and rub in.
Lay two slightly overlapping bacon slices on a board and place a chicken breast in the center.
Wrap bacon around the chicken, covering as much surface as possible, and secure with 2-3 toothpicks.
Repeat for remaining chicken breasts, tucking loose bacon ends underneath.
Preheat air fryer to 380°F (193°C) for 3-5 minutes and lightly spray the basket with cooking spray.
Place breasts in a single layer without touching, and cook for 10 minutes undisturbed.
Flip carefully with tongs and cook for 8-10 more minutes until internal temp reaches 165°F (74°C).
If bacon needs more crispness, increase heat to 400°F for 2-3 additional minutes.
Remove from air fryer, tent with foil, and let rest for 5 minutes before removing toothpicks and serving.