Instructions

• Preheat the oven to 425°F (218°C). Place a large oven-safe skillet nearby for later use.
• Cut the 2 lb chicken breasts in half lengthwise to make 8 thin cutlets. Place each cutlet between two sheets of plastic wrap or inside a quart-sized Ziploc bag and pound gently with a meat mallet or rolling pin until about 1/8" thick.
• Pat the cutlets dry with paper towels. Evenly sprinkle the 1 tsp garlic salt and 1/4 tsp black pepper over both sides of all cutlets.
• Reserve 2 oz of the shredded mozzarella for topping. You will have 6 oz of mozzarella remaining for the filling—divide that remaining 6 oz evenly among the 8 cutlets.
• Spoon 1 Tbsp pesto onto the center of each cutlet (1/2 cup pesto = 8 Tbsp total). On top of the pesto, place 2 thin tomato rings on each cutlet (2 medium tomatoes should yield 16 rings). Sprinkle each cutlet with its portion of the divided mozzarella.
• Tightly roll each cutlet around the filling and secure the seam and ends with toothpicks.
• Heat the oven-safe skillet over medium-high heat and add 1 Tbsp olive oil and 1 Tbsp unsalted butter. When the oil and butter are hot and shimmering, add the chicken roll-ups seam-side down.
• Sear the roll-ups until golden, about 4 minutes per side (about 8 minutes total on the stove), turning carefully so they brown evenly.
• Sprinkle the reserved 2 oz shredded mozzarella over the tops of the seared roll-ups. If using, scatter 1 cup cherry tomatoes around the roll-ups in the skillet.
• Transfer the skillet to the center rack of the preheated oven and bake at 425°F for 13–15 minutes, or until an instant-read thermometer inserted into the center of a roll-up reads 160°F.
• Remove the skillet from the oven. Take out and discard the toothpicks, let the roll-ups rest for a few minutes, then garnish with shredded fresh basil leaves if using. Serve warm.