Bring a large pot of salted water to a boil, and cook your pasta to al dente according to the package directions. Drain and rinse under cold water to prevent sticking. Set aside.
Preheat the oven to 350°F.
Drizzle the olive oil in a large pot or Dutch oven and heat over medium heat and add the butter (for the mac and cheese). Once the butter is melted and bubbling, add the flour and whisk to combine.
Slowly pour in the milk, whisking continuously. Add squash puree, garlic powder, onion powder, salt, and pepper.
Bring the mixture to a gentle simmer, and continue whisking until thickened. It should coat the back of a spoon.
Remove from heat and stir in the ½ cup Parmesan cheese. Whisk until completely melted. Add half of the shredded cheddar, whisk until completely melted, then repeat with the remaining cheddar.
Add the cooked pasta to the cheese mixture. Stir until all the noodles are completely coated.
Transfer to a 9×13 glass baking dish, and set aside while you make the breadcrumb topping.
In a small bowl, combine the panko, shredded Parmesan, and melted butter. Mix until the panko is evenly coated. Sprinkle the mixture over the mac and cheese, doing you best to it as evenly speard over the pan as possible. If you’d like, you can sprinkle additional shredded Parmesan on top too!
Bake for 15–20 minutes, or until the top is golden brown and the sauce is bubbly. At this I like to switch my oven to broil and broil my mac and cheese until the cheese is bubbly and golden on top. But you can easily skip this step.
Remove from the oven and let cool briefly before serving.
Enjoy!