Pat chicken cutlets thoroughly dry with paper towels. Season both sides evenly with Italian seasoning, garlic powder, kosher salt, and black pepper.

Heat 2 tablespoons of sun-dried tomato oil in a deep enameled cast-iron skillet or braiser over medium-high heat until shimmering. Add chicken cutlets in a single layer and sear for 4 to 5 minutes per side until deeply golden-brown and cooked to an internal temperature of 165°F (74°C). Transfer chicken to a clean cutting board and tent with foil to rest.

Reduce heat to medium. In the same skillet with pan drippings, add minced garlic and julienned sun-dried tomatoes. Sauté for 1 minute until fragrant, taking care not to scorch the garlic.

Pour in the chicken broth and heavy cream, scraping up the browned fond bits from the bottom of the skillet with a wooden spoon. Stir in the dry penne rigate pasta. Bring the liquid to a lively simmer.

Cover the skillet with a tight-fitting lid, reduce heat to medium-low, and simmer gently for 10 to 12 minutes, stirring every few minutes to prevent sticking, until the pasta is tender al dente and has absorbed most of the creamy broth.

Uncover the skillet and reduce heat to low. Stir in the freshly grated Parmigiano-Reggiano until melted into a silky, glossy sauce. Fold in the fresh baby spinach in two batches, stirring for 1 to 2 minutes until just wilted into the hot pasta.

Slice the rested seared chicken cutlets into 1/2-inch strips. Arrange the warm chicken over the creamy penne, scatter fresh torn basil and extra grated parmesan across the top, and serve immediately with crusty sourdough bread.