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Step 1
Heat oven to 375ºF.
Step 2
Bake the potatoes directly on the middle rack of the oven until very tender, about 1 hour. At the same time, place the squash, flesh-side down, on a half-sheet pan and roast until very tender, about 45 minutes.
Step 3
Split the potatoes and allow to cool slightly, or until they can be handled safely. Don't let them cool completely. Scoop the flesh of the potatoes into a large mixing bowl and smash with a potato masher.
Step 4
Scoop the squash from its skin and add to the potatoes. You should have approximately 10 ounces of potato and 20 ounces of squash. Mash them together with a hand masher until mostly smooth. There may be some small lumps. Mix in the egg, salt, and nutmeg. Then add the flour and mix with a large wooden spoon until a soft dough forms. Do not do this in a mixer, it will overwork the dough. Add more flour by the spoonful if the dough is still too moist.
Step 5
Turn dough out onto a clean, floured counter and divide into 8 portions. Roll each portion out into ropes, about 2 feet long, and cut into 1-inch pieces. Line the pieces up on a floured half-sheet pan as you work. At this point, you could freeze them on a half-sheet pan until solid, then transfer to zip-top bags and store in the freezer for up to 1 month.
Step 6
In a large pot of boiling, salted water, gently drop in the dumplings about 2 dozen at a time; don't overcrowd. As they begin to float, 3 to 4 minutes, remove them with a slotted spoon and toss them into an ice bath for 1 minute.
Step 7
Drain the dumplings, pat dry with a clean kitchen towel, and toss in a little oil. Store loosely in a large container until ready to use. The dumplings can be cooked and stored in the fridge this way for up to 3 days.
Step 8
To serve: Melt 1 tablespoon of butter in a large sauté pan over high heat. Cook until the butter begins to foam and turn brown. Add 2 teaspoons sage leaves and 1 cup of dumplings. Cook until the dumplings are heated through, about 1 minute. Repeat until you have desired amount of servings. Plate and top with freshly grated Parmesan.