Preheat the oven to 400 degrees F. Line a small baking sheet or pan with parchment paper.
Season the chicken cutlets with salt and pepper. Lay them down in a row on the baking sheet.
Top each one with 1 tablespoon of pesto and spread from edge to edge.
Cut the roasted red peppers in half and place one on each chicken cutlet closest to the skinnier side.
Sprinkle ⅓ cup mozzarella over each one.
Roll the cutlets up from the smallest end and secure with toothpicks. Sprinkle the Italian seasoning over them.
Bake until cooked through 18 - 25 minutes depending on their size/thickness.
Remove the toothpicks and discard.
To serve top each one with the remaining tablespoon of pesto.