Preheat oven to 400F.

Set the chicken breasts on a cutting board. Place one hand flat on one chicken breast and extend your fingers away from the board for safety. With your knife blade held parallel to the cutting board, slice the chicken breast horizontally, cutting *almost* to the other side. Be careful not to slice all the way through. Repeat with the remaining chicken breasts.

Stuff the chicken breast with 4 asparagus spears. Repeat with the remaining chicken breasts. Evenly season both sides with Italian seasoning. Lay two slices of prosciutto side-by-side on a cutting board. Place the stuffed chicken breasts overtop and wrap tightly with the prosciutto.

Add arrowroot starch to a bowl. Dredge the chicken all over with the starch and pat off the excess.

Preheat a large, oven-safe skillet over medium-high heat. Add the olive oil and heat until shimmering. Add the chicken breasts and cook, undisturbed, until golden brown, around 3 minutes. Flip and transfer the pan to the oven. Roast for around 12 minutes or until the thickest part of the breast registers 165F on a digital thermometer. Remove from heat and serve immediately with side of choice.