While the water comes to a boil, cut the chicken breast into 1-inch chunks and combine the garlic powder, Italian seasoning, kosher salt, and pepper in a small bowl. Toss the chicken with the olive oil and spice mixture until evenly coated, allowing the seasoning to adhere. I like to let the seasoned chicken sit for a few minutes while you finish prepping—this helps the flavors penetrate the meat slightly before cooking.

Bring a large pot of salted water to boil and cook the pasta according to package directions until al dente, then drain and rinse with cold water to stop the cooking process. While the pasta cooks, heat a skillet over medium-high heat and cook the seasoned chicken chunks for 5 minutes on the first side until golden, then flip and cook for another 3-5 minutes until cooked through. This parallel cooking saves time—the chicken and pasta will both finish around the same time.

In a medium bowl, whisk together the Italian dressing, Greek yogurt, and pesto until smooth and well combined. The Greek yogurt creates a creamy, protein-rich base that makes this dressing both rich and slightly lighter than a traditional mayo-based version. Set the dressing aside until ready to assemble.

While the chicken cools slightly, halve the cherry tomatoes lengthwise (this exposes more surface area to absorb the dressing), finely dice the red onion, tear the fresh basil into 1/2-inch pieces, and set each aside. I find that halving the tomatoes lengthwise rather than just cutting them in half makes a noticeable difference in how well they soak up the dressing.

In a large bowl, combine the cooled pasta from Step 2, cooked chicken from Step 2, halved cherry tomatoes, diced red onion, and torn basil from Step 4. Pour the pesto dressing from Step 3 over the mixture and toss gently but thoroughly until everything is evenly coated. Add the 1/3 cup of Parmesan and stir once more to distribute.

Divide the pasta salad into serving bowls or plates. Top each portion with an additional sprinkle of Parmesan cheese and fresh cracked pepper to taste. Serve immediately or chill for up to 2 hours before serving—the flavors will continue to meld as it sits.