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Preheat griddle on low. While griddle is preheating, begin to heat a medium pot of water on the stovetop. Water level should be just high enough to boil the ravioli. (You should begin heating the pot of water on the stovetop and then carefully transfer it to the griddle to cut down on boiling time.)
Add 4 tablespoons unsalted butter to a small saucepan on the griddle. Melt the butter, taking care that it does not burn. When butter is melted, add 3 sage leaves and continue to cook down to create a brown butter. Browned bits will develop on the bottom of the saucepan. You may need to move the pan on and off the griddle to prevent the butter from burning.
While butter is melting, begin cooking the Italian sausage on the griddle. When sausage is about half way cooked through, move it over to the side of the griddle to continue to cook.
Saute the cubed butternut squash on the griddle. Use your spatulas to direct the excess sausage grease into the squash for extra flavor. After a few minutes of sautéing, add a bit of water and place a dome over the squash. Allow the squash to steam, stirring occasionally.
When sausage is almost cooked through, add the sliced shallot and garlic. Mix together to combine, and continue to cook the sausage until done. When sausage is done, add it to the cooked butternut squash and combine. Continue to saute butternut squash and sausage mixture until squash is tender and done to your liking. You may dome the sausage and squash mixture to help speed up the cooking time.
While squash finishes cooking, add the ravioli to the pot of boiling water and cook per package instructions.
When squash is done cooking, add baby spinach and cranberries to the sausage and squash mixture. Saute all ingredients until cranberries are heated and spinach is slightly wilted.
When pasta is done, use a spider strainer to add pasta to the other ingredients on the griddle, reserving the pasta water. Remove sage leaves from the brown butter and discard. Pour the brown butter over the sausage and squash ravioli mixture. Toss to combine. You may add some of the pasta water (about ¼ - ½ cup) to loosen up the pan sauce if you wish.
Allow the pasta to cook for about 2 more minutes with the other ingredients for all of the flavors to marry. Add about 3 oz of grated parmesan. Stir to combine. Add additional pasta water as needed to loosen sauce. Transfer sausage and squash ravioli to serving plates and top with more parmesan before serving.