Sopaipillas (Chilean Fried Pastries)

Instructions

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1. 1 For the Sopaipilla Dough: Adjust oven rack to middle position and preheat oven to 400°F (205°C).
2. 2 On a rimmed baking sheet, brush butternut squash with oil and place cut side down on baking sheet. Roast, flipping squash to cut side up halfway through, until tender and golden brown at edges, about 45 minutes. Let cool slightly, about 5 minutes.
3. 3 Scoop 8 ounces cooked squash flesh and transfer to a food processor, high powered blender, or immersion blender jar. Save remaining roasted squash for another use. Process squash, scraping down sides of processor bowl as needed, until completely smooth, about 2 minutes.
4. 4 In a large bowl, whisk flour, baking powder, and salt until combined. Using a wooden spoon, stir in squash puree and melted shortening until combined and some lumps form.
5. 5 Stir in warm water, 1 tablespoon at a time, until a rough ball forms (total added water may range from 3 to 6 tablespoons).
6. 6 Transfer dough to a clean work surface and gently knead by hand until dough feels smooth but still firm, 1 to 2 minutes; do not over-knead the dough. Wrap in plastic wrap and let rest on counter for 15 minutes.
7. 7 Unwrap and transfer sopaipilla dough to a lightly floured work surface. Using a rolling pin, roll dough into a 16-inch circle, about 1/4-inch thick. Using a 3-inch round cutter, cut circles from the dough.Transfer dough rounds to a parchment-lined baking sheet. Dough scraps may be gathered together, rerolled to a 1/4-inch thickness, and cut into more rounds. You should have about 26 dough rounds total.
8. 8 Using a fork, prick each dough round three times (making sure to poke all the way through the dough as this reduces dough from puffing too much while frying).
9. 9 Set wire rack in a rimmed baking sheet. Line rack with a double layer of paper towels. In a large Dutch oven, heat oil over medium-high heat to 350°F (175°C). Gently place 5 sopaipillas in hot oil. Cook, adjusting burner as necessary to maintain oil temperature around 350°F (175°C) degrees, until golden brown on undersides, about 2 minutes. Using a spider skimmer, gently flip sopaipillas and fry until second sides are browned, about 2 minutes. Transfer sopaipillas to prepared rack. Return oil to 350°F and repeat with remaining sopaipillas in batches of 5 at a time.
10. 10 For Sopaipillas Pasadas: In a large pot, stir together chancaca, granulated sugar, orange peels, cinnamon sticks, cloves and 1 1/2 quarts (1.4L) water. Bring to a boil over high heat, then reduce heat to low and simmer, stirring occasionally, until chancaca is dissolved.
11. 11 Whisk cornstarch slurry to remix. Return syrup to a boil over high heat and pour cornstarch slurry into boiling syrup while whisking. Simmer, stirring occasionally, until thickened, about 2 minutes. Remove from heat.
12. 12 Transfer fried sopaipillas to the hot syrup. Soak sopaipillas until softened to desired consistency, 15 to 90 minutes (see notes). Return to a simmer before serving in individual bowls. Serve 2 to 4 sopaipillas per person with additional hot syrup ladled over top.
13. 13 For Sopaipillas with Pebre: In a medium bowl, stir together all the pebre ingredients and season with salt to taste. Let stand at room temperature until flavors meld and vegetables begin to soften, about 20 minutes. Serve pebre alongside freshly fried and crispy sopaipillas.