Make the crust: In a large bowl, whisk the gluten-free flour, almond flour, arrowroot, and salt. Cut in the cold butter with a pastry cutter or your fingers until pea-sized bits form.
Beat the egg and add it. Drizzle in ice water, 1 tablespoon at a time, until the dough holds together when pressed.
Chill the dough: Divide dough into two disks, wrap, and chill for 45–60 minutes. Cold dough is key for a flaky crust and easier rolling.
Cook the filling: In a skillet over medium heat, combine apples, dates, maple syrup, lemon juice, cinnamon, nutmeg, vanilla, and salt.
Cook, stirring, for 5–7 minutes until the apples soften. Sprinkle in arrowroot and cook 1–2 minutes until glossy and thickened. Cool completely.
Prep the workspace: Heat oven to 375°F (190°C).
Line a baking sheet with parchment. Lightly dust a surface with gluten-free flour or roll between two sheets of parchment.
Roll and cut: Roll the first dough disk to about 1/8 inch thick. Using a 4–5 inch round cutter (or a small bowl), cut circles.
Gather and reroll scraps. Repeat with second disk.
Fill the pies: Place 1–2 tablespoons of cooled filling in the center of each circle. Brush edges lightly with water.
Fold into half-moons and press edges to seal. Crimp with a fork.
Vent and glaze: Place pies on the lined sheet. Cut a small slit on top of each.
Brush with egg wash and sprinkle with coconut sugar if using.
Bake: Bake 18–22 minutes, until golden and crisp. If using coconut oil, they may need an extra 2–3 minutes. Cool on the sheet for 5 minutes, then transfer to a rack.
Serve: Enjoy warm or at room temperature.
The filling sets as it cools, making them easy to pack.