Bring a large pot of salted water to a boil.
Cook the ravioli according to package directions, adding the prepared squash to the pot during the final 2 minutes of cooking time.
Drain everything well and return the ravioli and squash to the warm pot.
While the pasta cooks, create the quick pesto.
In a blender, combine the fresh baby spinach, torn basil, Caesar vinaigrette, and water.
Cover and blend until the sauce is completely smooth, pausing to scrape down the sides of the blender with a spatula if needed.
Pour the vibrant spinach pesto over the warm ravioli and squash in the pot.
Toss gently until everything is evenly coated in the creamy sauce.
Serve immediately, sprinkled with extra shredded Parmesan cheese, if desired.