Bring a pot of water to a boil and season with kosher salt. Cook the pasta according to package directions or until al dente, rinse, drain, and cool. Place in a large bowl and set aside.
Meanwhile, preheat an oven or toaster oven to 400° degrees. Place the tomatoes on a small baking tray, drizzle with extra virgin olive oil and toss lightly. Season with kosher salt and freshly ground black pepper and roast until the tomatoes have softened and started to burst, about 12-15 minutes.
Stem and chop the kale into small pieces and add to the pasta with the cherry tomatoes. Pour about half of the bottle of Caesar dressing onto the salad and toss gently, adding more dressing if desired. Sprinkle with Parmesan cheese and season with freshly ground black pepper. Refrigerate for an hour before serving.