Preheat the oven. Set your oven to 400°F (200°C) so it has time to fully heat while you prepare the chicken. This temperature helps finish the chicken evenly after searing, keeping the outside nicely browned while the inside cooks through.
Season the chicken breasts thoroughly. Place the 4 skinless boneless chicken breasts on a clean cutting board. Sprinkle them on all sides with Italian seasoning mix, garlic powder, smoked paprika, sea salt, and pepper. Take a moment to rub the seasonings gently over the surface of each breast so they stick well. This step builds flavor from the very beginning, so aim for an even coating rather than seasoning only the top.
Slice each chicken breast to create pockets. Working with one chicken breast at a time, use a sharp knife to slice it lengthwise to form a pocket. The goal is to create a space for the filling without cutting all the way through. Start from the thicker side of the breast and carefully open it like a book. Go slowly and keep your knife parallel to the cutting board, checking as you go so the bottom edge stays intact. Repeat for all four breasts, making sure each pocket is large enough to hold the filling.
Prepare the filling components. Make sure your 12 asparagus stalks are ready to use. Since each chicken breast gets three asparagus stalks, it helps to divide them into four small bundles of three. Next, have the sun-dried tomatoes ready (they will be chopped as part of the stuffing step). Finally, set out the 4 slices of mozzarella cheese so each chicken breast gets one slice.
Stuff each chicken pocket. Open the pocket of the first chicken breast and place three asparagus stalks inside, laying them lengthwise so they fit neatly from end to end. Add the chopped sun-dried tomatoes into the pocket, distributing them around the asparagus so you get a bit of tomato flavor in every bite. Then add one slice of mozzarella cheese into the pocket. Tuck the cheese in so it sits close to the asparagus and tomatoes, helping everything stay together as it melts during cooking. Repeat the same process for the other three chicken breasts: three asparagus stalks, chopped sun-dried tomatoes, and one mozzarella slice per breast.
Secure the openings with toothpicks. Once each chicken breast is stuffed, close the pocket by gently pressing the top flap back into place. Use toothpicks to secure the opening so the filling stays inside during searing and baking. Insert the toothpicks across the seam, like little stitches, spacing them out enough to hold the pocket closed. Keep the toothpicks visible so they’re easy to spot later.
Asparagus Stuffed Chicken Breast 4
Sear the stuffed chicken in olive oil. Place a skillet over medium-high heat and add olive oil. When the oil is hot, carefully lay the stuffed chicken breasts in the pan, seam-side up first if possible to help the pocket stay closed. Sear until golden brown, about 3–5 minutes per side. Let the chicken cook without moving it too much so the surface can develop color. When it’s ready to flip, it should release more easily from the pan. Turn each breast and sear the second side for another 3–5 minutes, aiming for an evenly browned exterior. This step is important because it adds flavor and gives the chicken a more appealing texture before it goes into the oven.
Bake until fully cooked. After searing, transfer the chicken to the oven and bake for 15–20 minutes, until the chicken is fully cooked. Baking finishes the center gently, allowing the mozzarella to melt inside the pocket while the asparagus and sun-dried tomatoes warm through. Keep the stuffed pockets facing upward as much as possible so the filling stays in place.
Serve. Once the baking time is complete and the chicken is fully cooked, remove it from the oven. The chicken should look golden on the outside, with the filling hot and melted inside. Before serving, remember to remove the toothpicks so each portion is ready to eat comfortably.
