Preheat your air fryer or oven to 390F.
Place a slice of ham and cheese together and roll it up like a cigar to help with stuffing. Set aside.
Lay the chicken breasts on a cutting board. If the chicken is much thicker on one end pound it flat between two pieces of plastic wrap to a more even thickness.
Trim any cartilage or excess fat from the chicken breast.
With a sharp pairing knife, cut a slit or pouch in the chicken breast deep enough to hold the ham and cheese.
Stuff the ham and cheese cigar into the pouch you sliced into the chicken breast.
Using shallow bowls or paper plates, make a dredging station for breading the chicken with both oil and breadcrumbs in separate vessels.
Dip and coat the chicken in oil than in breadcrumbs.
Optional: allow the chicken to rest at room temperature for 30 minutes
Place the chicken in your air fryer.
Cook the chicken in the air fryer checking periodically.
Cook the chicken until it reaches a minimum internal temperature of 165F
Remove from air fryer and enjoy-