Place the chicken pieces in a mixing bowl and season thoroughly with Italian seasoning along with a generous pinch each of kosher salt and freshly cracked black pepper, then toss until evenly coated. Fill a medium pot with water, bring it to a rolling boil, and add about a tablespoon of salt. Cook the penne until al dente according to the package directions, generally 8 to 9 minutes. As the pasta cooks, warm the olive oil in a spacious non-stick skillet set over medium-high heat. Add the seasoned chicken and sauté, turning occasionally, until the pieces turn golden on the outside and are fully cooked through, approximately 7 to 8 minutes. Reserve a cup of the starchy pasta water before draining the pasta. Reduce the skillet’s heat and fold the cooked pasta into the pan with the chicken, then stir in the heavy cream, parmesan, and sun dried tomatoes until everything melds together. Should the mixture appear too dry, gradually add a splash of the reserved pasta water until the sauce reaches a smooth, glossy consistency. Remove the pan from the heat and gently stir in the basil pesto, finishing with an extra sprinkling of grated parmesan, a pinch of red pepper flakes, and a scattering of fresh basil leaves. Serve promptly.