3 tablespoons olive oil, plus more for baking dish and sheet
Coarse salt and ground pepper
8 wide lasagna noodles
1/2 butternut squash (about 1 pound), peeled, seeded, and cut into 1-inch chunks
2 shallots, chopped
1/4 cup plus 2 tablespoons milk
1 teaspoon finely chopped fresh sage leaves, plus 8 to 10 whole leaves
1/8 teaspoon ground nutmeg
2 cups ricotta (15 ounces)
3/4 cup grated Parmesan
Preheat oven to 350 degrees. Lightly oil a 2-quart or 8-inch square baking dish. In a large pot of boiling salted water, cook pasta until al dente. Using tongs, transfer pasta to a lightly oiled rimmed baking sheet. Add squash to boiling water and cook until tender, about 10 minutes. Drain squash and transfer to a bowl.
In a small skillet, heat 1 tablespoon oil over medium. Add shallots, season with salt and pepper, and cook until soft, about 5 minutes. Transfer to bowl with squash and add 2 tablespoons milk, chopped sage, and nutmeg; season with salt and pepper. Mash with a fork until a rough puree forms.
Spread 1/4 cup squash mixture crosswise down the middle of each lasagna noodle; roll up noodle and place, seam side down, in baking dish. In a bowl, combine ricotta, 1/2 cup Parmesan, and 1/4 cup milk and season with salt and pepper. Spread ricotta mixture over cannelloni and top with cup Parmesan. Bake until warmed through, about 25 minutes. Broil until top is browned, 2 to 3 minutes.
Meanwhile, in a small skillet, heat 2 tablespoons oil over medium-high. Fry whole sage leaves until crispy, 15 to 20 seconds. Drain on paper towels. Serve cannelloni topped with fried sage.
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