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1
Dough
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2
Pulse flour, sugar, and salt in a food processor to combine. Add butter; pulse until mixture resembles coarse cornmeal (no big pieces of butter should remain). With motor running, slowly drizzle 1/2 cup ice water through feed tube. Pulse until dough just begins to come together.
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3
Divide dough in half. Form each half into a ball; flatten into disks. Wrap each disk tightly in plastic. Chill for at least 2 hours. DO AHEAD Dough can be made 2 days ahead. Keep chilled. Let stand at room temperature for 15 minutes to soften slightly before rolling out.
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4
Filling And Assembly
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5
Combine cranberries, sugar, orange zest and juice, and tapioca in a medium saucepan. Scrape in seeds from vanilla bean; add bean. Let stand for juices to accumulate, about 10 minutes, then cook over medium heat until mixture comes to a simmer and begins to thicken, 5-6 minutes. (Some cranberries will have burst.) Let cool completely. DO AHEAD Cranberry filling can be made 5 days ahead. Cover and chill.
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6
Line two baking sheets with parchment paper; set aside. Working with 1 disk at a time, roll out dough on a lightly floured surface until very thin, about 1/16-inch thick. Using cookie cutter, cut out 16 circles.
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7
Brush edges of 8 circles with beaten egg. Place 1 heaping tablespoon filling in center of each egg-washed circle. Top with remaining circles to form 8 pies. Using a fork, crimp 1/4-inch around edges to seal. If desired, use cookie cutter to clean edges. Repeat with remaining dough, egg, and filling.
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8
Divide pies between prepared sheets; chill for 45 minutes. DO AHEAD Pies can be made 2 hours ahead. Cover; keep chilled.
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9
Preheat oven to 425AAAAu00b0. Working with 1 baking sheet of pies at a time, score dough, forming a small X in the center of each pie. Brush tops of pies with beaten egg and sprinkle with raw sugar.
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10
Bake pies until crust is golden brown and filling bubbles out of Xs, 17-20 minutes. Let cool on baking sheet for 5 minutes; transfer to a wire rack and let cool completely.
