For the dough

1. Mix dry ingredients and butter. Pulse flour, sugar, and salt in a food processor to combine (see Note 2). Add butter; pulse until mixture resembles coarse crumbs and no big pieces of butter remain.
2. Add water. Drizzle 4 tablespoons ice water evenly over the mixture and pulse in processor until incorporated. Squeeze a small handful of dough together. If it doesn’t hold together, add more ice water, ½ tablespoon at a time, pulsing until just incorporated, then test again. You may not need all the water.
3. Chill dough. Gather dough together and divide dough in half. Form each half into a ball then flatten into a ½-inch thick disk. Wrap dough in plastic and chill for at least 2 hours.

For the filling

1. Make filling. Combine cranberries, sugar, orange zest, orange juice, and tapioca in a medium saucepan. Scrape in seeds from vanilla bean; add bean. Cook cranberry mixture over medium heat until mixture comes to a simmer and begins to thicken and about half the cranberries have burst, about 6 minutes. Let cool completely (see Note 3). Discard vanilla bean pod.

For assembly

1. Roll and cut dough. Working with 1 disk at a time, roll out dough on a well floured surface until very thin, about 1/8 to 1/16 inch thick. If the dough is too firm to roll out after refrigerating, allow it to sit at room temperature for 5 minutes before rolling it out. Using a 3-inch diameter cookie cutter, cut out as many circles as possible (see Note 4). Store the cut rounds in the refrigerator on a baking sheet or board while rolling and cutting the second ball of dough. You can layer the rounds between sheets of parchment paper, if necessary. You should end up with 40-48 cut rounds depending on how thin/thick you roll out your dough. Be sure to cut an even number of rounds. You may also need to gather the scraps of dough and re-roll to get enough cut rounds. If the dough gets too soft to work with, put it back in the refrigerator or freezer until it firms up again.
2. Prep oven and pans. When ready to bake the pies, heat oven to 425 degrees F and line 2 baking sheets with parchment paper or silicone liner.
3. Assemble pies. Place half the cut rounds of dough on the two baking sheets. Brush edges of the circles with beaten egg. Place 1 heaping tablespoon of filling in center of each egg-washed circle. Top with remaining rounds of dough and gently press the edges down to form pies. Using a fork, crimp 1/4-inch around edges to fully seal. With the tip of a small paring knife, cut a small X in the center of each pie. Brush tops of pies with beaten egg and sprinkle generously with raw sugar.
4. Bake. 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.