Bring 8 quarts of water to a boil in a large pasta pot. Cook manicotti pasta to al dente then drain under cold water.
Preheat oven to 350ºF. Mix the sharp and smoked cheddar shredded cheeses together in a large bowl.
For the pesto, chop the oregano and basil then add the chopped herbs to a food processor along with the pine nuts, milk, parmesan cheese and salt. Process the pesto into a nice paste-like consistency.
For the topping, in a medium bowl, mix together dried basil and oregano, chili flakes, parmesan cheese and breadcrumbs.
In a 9x13-inch baking dish, lay down one layer of manicotti pasta. Open the manicotti pasta tubes creating a flat pasta similar to lasagna. Lay a flat layer of manicotti on the bottom of the baking dish then a layer of the cheddar cheese blend then another layer of manicotti pasta and another layer of cheese. Add another layer of manicotti but this time, before you add another cheese layer, spread a layer of the pesto on the manicotti then add another layer of cheese on top of the pesto. Add a final layer of manicotti noodles and cheese.
Spread the crunchy topping over the four-layer manicotti casserole and pour 1/4 cup milk along the edge of the pan. Bake for 30-35 minutes.
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