Pie crust: In a food processor, briefly pulse together the flour, sugar and salt. Add the butter and pulse until mixture forms chickpea-size pieces (3 to 5 one-second pulses). Be sure the butter is cold at this step. Add ice water 1 tablespoon at a time, and pulse until mixture is just moist enough to hold together. You should be able to pinch it & it stays together.

Form dough into two balls, wrap with plastic and flatten into disks. Refrigerate at least 1 hour to 24 hours before rolling out and baking.

Combine the cranberries, sugar, orange juice, vanilla and starch in a medium saucepan. Cook over medium heat until the mixture comes to a simmer. Cook another 6 minutes, some cranberries will burst and mixture will start to thicken. Transfer the cranberries to a bowl and cool to room temperature. Sauce will thicken as it cools. DO AHEAD: You can make this filling up to 5 days ahead of when you want to use it.

Pre-heat the oven to 375 degrees Fahrenheit with the racks in the middle. Line two baking sheets with parchment paper; set aside. Remove the dough from the refrigerator & let it sit out a few minutes until just pliable. On a lightly floured surface, roll out one dough disk into 1/8 inch thickness. Punch out heart or round shapes I used a 4 inch heart cookie cutter.

Spoon 1 heaping tablespoon of the cranberry mixture onto the middle of a dough heart. Wet the rim of the disk with some egg wash Place another heart on top. Crimp the edges with a fork or your fingers. Continue with the rest of the dough and filling. Place shapes on 2 cookie sheets. Refrigerate pies for 45 minutes.
You will likely have filling left over, it’s great on pancakes or mixed into oatmeal.

Remove pastry With a sharp knife, make a X on the top to vent. Brush on egg wash and dust with some sugar.

Bake for 30-35 minutes, until the edges are golden brown. Let cool on baking sheets for 5 minutes, transfer to a wire rack and let cool completely.