Prepare the Chicken. Place each boneless, skinless chicken thigh on a cutting board. Lay it out flat, removing any undesirable pieces.
Stuff the Filling. Lay 4–5 asparagus spears onto each chicken thigh. They should fit snugly but comfortably. Place slices of cheese on the chicken thighs with the asparagus. Roll the thigh over with your hands to secure the cheese and asparagus. Carefully roll each chicken thigh in long strips of thin bacon, leaving the ends on the bottom of the thigh to help secure it in place. If you prefer extra security, use toothpicks to hold it shut.
Season the Chicken. Sprinkle garlic powder, onion powder, paprika, Italian seasoning, salt, and pepper evenly on all sides. Season generously. This is what gives the outside that golden, savory crust.
Air Fry to Perfection. Preheat your air fryer to 375°F. Place the stuffed chicken thighs in the basket in a single layer. Cook for 15–18 minutes, flipping halfway through. You’ll know they’re done when the chicken reaches an internal temperature of 165°F, the exterior is golden and crisp, and the cheese begins to lightly ooze from the seam.
Rest & Serve. Let the chicken rest for 5 minutes before slicing. Resting keeps all the juices locked inside instead of spilling onto the cutting board. Slice, plate, and enjoy the gorgeous cross-section of vibrant asparagus and melted cheese.