Squash & Brown Butter Tortelli With Brussels Sprouts & Balsamic

Directions

1. Roast the squash
   
   Preheat the oven to 375°F.
   
   In a large bowl, toss the squash with olive oil, salt, and pepper and transfer to a baking dish or foil-lined baking sheet.
   
   Roast until very tender, about 45 minutes, stirring every 15 minutes. You’re looking for the squash to be a little overcooked so it’ll puree nicely.
   
   While the squash roasts, make the brown butter, balsamic reduction, and the pasta dough; when the squash is done, allow it to cool completely. You should end up with about 450 grams (2 1/4 cups) of cooked squash.
2. Brown the butter
   
   To maximize efficiency, combine the butter for the filling and the sauce—150 grams, or 3/4 cup—into a small, heavy-bottomed saucepan.
   
   Cook over medium heat, stirring constantly, until the milk solids separate, froth, and just start to turn golden, 5 to 7 minutes.
   
   Remove from the heat and continue to stir briefly until the color deepens a bit more, then transfer to a heat-proof bowl to stop the cooking. Allow it to cool a bit.
   
   Set aside 50 grams (1/4 cup) of the brown butter for the filling and the remainder for the sauce. If prepping ahead, you can store the brown butter for the sauce in an airtight container in the refrigerator and reheat when needed (it’ll last for up to two weeks).
3. Make the balsamic reduction
   
   Add the balsamic vinegar to a small saucepan over medium heat. Bring to a gentle boil, then reduce the heat to medium-low and simmer, stirring occasionally, until thickened, 10 to 15 minutes. It should coat the back of a spoon.
   
   Remove from the heat and set aside—it’ll continue to thicken as it cools. If prepping ahead, store the reduction in an airtight container in the refrigerator until needed for the finished dish (it’ll last for several weeks).
   
   Note: If the reduction hardens or thickens too much once it’s cooled, gently reheat it with a small amount of water to loosen so it’s easy to drizzle.
4. Make the pasta dough
   
   Make the pasta dough by hand according to the well method (see my master pasta dough tutorial that teaches you how: https://food52.com/recipes/83340-semolina-pasta-dough-recipe).
   
   Alternatively, add the flour, eggs, and yolks to the bowl of a food processor with the steel blade attachment. Pulse together until beads of dough start to form and come together, about 30 seconds. Transfer the dough to a flat, ideally wooden surface, bring it together and knead for 5 to 10 minutes until smooth and firm.
   
   Wrap the dough tightly in plastic and allow it to rest at room temperature for about 30 minutes.
5. Finish the filling
   
   When the squash is cool, transfer it to a paper-towel lined baking sheet and pat it dry to remove as much excess moisture as possible.
   
   Add the squash to the bowl of a food processor with the steel blade attachment. Pulse until very smooth and creamy. Follow with the 50 grams (1/4 cup) cooled brown butter, cheeses, nutmeg, and a generous pinch of salt and pepper. Pulse again until well-combined.
   
   Adjust seasoning to taste, transfer the filling to a bowl or piping bag, and refrigerate it until ready to use. If prepping ahead, you can store the filling in an airtight container in the refrigerator for up to 3 days.
6. Make the tortelli
   
   Line a baking sheet with semolina flour, cornmeal, or a dry dish towel and keep it nearby.
   
   Cut off a quarter of the pasta dough and re-wrap the remainder immediately.
   
   If you have a pasta machine: Flatten the dough with the heel of your hand until it’s about 1/4-inch thick. Set your pasta machine to its thickest setting and roll the dough through once—it will be tapered at the ends. Fold the ends into the center like an envelope so the width of the pasta sheet is similar in width to the pasta roller. Line up the widths and roll the dough through the thickest setting once more so the result is an even rectangle.
   
   Continue rolling the pasta sheet through the machine once on each progressive setting until you can see your hand through it but it’s still sturdy (a bit like leather), about setting 6 or 7 on a Marcato Atlas 150 manual roller or KitchenAid attachment. If the dough is at all sticky going through the machine, dust it with a light layer of ‘00’ or all-purpose flour on both sides.
   
   If you’re rolling by hand: Roll the portion of dough with a rolling pin into as thin a square or rectangle as possible—it’s a workout! While you’re aiming for about a millimeter thick, don’t stress and do the best you can!
   
   Once you have a long, thin sheet of pasta, lay it on a wooden surface and trim the ends of any uneven areas, then ball up the scraps and wrap them in plastic to rehydrate. If you don’t have a wooden surface, dust some flour on the bottom of the pasta sheet and your countertop to prevent sticking.
   
   With a sharp knife or pasta wheel, cut the sheet in half lengthwise so you have two rows. Then cut the rows crosswise into squares, as evenly as possible (they should be about 2 1/2 inches).
   
   Spoon or pipe about a teaspoon of filling in the center of each square, leaving a generous rim of dough around it. Piling the filling upwards instead of outwards will ensure the tortelli will be well-filled but still able to seal properly.
   
   If the dough is dry, add a small amount of water with your finger on two adjoining edges of the square.
   
   Fold each square into a triangle, meeting opposite points first and then gently pressing out any air around the filling on each side. Once the filling is encased, go back over the edges with your fingers and press firmly to seal. If desired, trim the edges with a fluted pasta cutter.
   
   Place each finished piece on the prepared baking sheet in a single layer. Repeat the process with the remaining dough.
   
   Note: If prepping ahead, flash-freeze the tortelli on the baking sheet until mostly solid, 20 to 25 minutes (you may need to do this in batches; make sure not to leave them uncovered in the freezer for too long or they’ll crack!). Dust off any excess semolina flour and transfer them to a freezer-safe container or bag until ready to cook—they’ll last for up to a couple of months.
7. Cook the Brussels sprouts
   
   Trim the bottom ends off the Brussels sprouts and remove any discolored outer leaves. Cut them in half. If the sprouts are very large, cut them in quarters.
   
   Heat 1 to 2 tablespoons of olive oil or clarified butter in a skillet over medium-high heat. Add the sprouts, cut-side down, and sprinkle with salt. Cook, shaking the pan occasionally, until browned on the cut-side, vibrant green elsewhere, and still crisp in texture, 5 to 8 minutes. If the sprouts start to brown too quickly, turn down the heat.
   
   Transfer to a plate and adjust seasoning with salt and pepper as needed.
8. Finish the dish
   
   Bring a large pot of water to a boil.
   
   Reheat the remaining brown butter and the balsamic reduction in small saucepans over low heat. Loosen the reduction with a tablespoon or two of water if needed.
   
   Salt the pasta water well and add the tortelli, making sure to dust off any excess semolina flour or cornmeal. Cook 2 to 3 minutes or to your liking, tasting for doneness. If you’re using frozen tortelli, cook them straight from the freezer for 3 to 4 minutes.
   
   While the tortelli cook, turn up the heat on the brown butter to medium. Add a few spoonfuls of pasta water (watch out, it’ll sizzle and foam!) and stir vigorously to combine into a glossy, emulsified sauce. If substituting sage leaves for Brussels sprouts, add them to the butter sauce and cook them briefly, continuing to stir. Remove from the heat and season with salt to taste.
   
   With a slotted spoon, transfer the tortelli to a large platter. Arrange the Brussels sprouts around the pasta and spoon the butter sauce on top. (If preferred, make the butter sauce in a large saute pan, transfer the pasta directly to the pan, and toss to coat. This is easier for smaller portions). Finish with a generous dusting of Parmigiano-Reggiano and a drizzle of the balsamic reduction. Serve immediately and enjoy!