Gather all the ingredients, and get everything measured and prepped. You will want the pre-made pie dough to be defrosted, unless it's homemade. Dough should be cold.
Preheat oven to 350°F, and line a cookie sheet with parchment paper. Set aside.
Heat a medium pot, add the diced apples, brown sugar, cinnamon, and butter, and cook on medium heat until it starts to bubble, and thicken. About 15 minutes. If the juices are runny, add a teaspoon of flour to thicken, stir and cook for 1-2 minutes. Add more if needed, and repeat step. Remove from heat, and let cool.
Roll out the pie crust on a lightly floured surface. Then press the apple cookie cutter into the dough. Place the apple cut outs on a plate, and into the refrigerator to keep cold. Re-roll the remaining dough, and repeat steps. Be sure to have an even number for the top and bottom of the hand pies. (about 16 total)
Place the apple cut outs on the parchment paper about 2" apart. Spoon 1 tablespoon of the filling into the middle of each one. Then dip the pastry brush into the egg wash, and brush the inside edge going around the filling. (This will keep the edges sealed.)
Next, place the top apple cut outs over the filling, lining the edges up so the shape seals evenly. Gently press around the edges, and pressing out the edges any air bubbles. Then, crimp the edges with a fork.
Again dip the pastry brush in the egg wash, and brush the tops and edges of the hand pie. With a knife make 3 small slits on the top of the pie, or poke a couple times with a fork for venting.
Place in oven and bake 12-15 minutes, or until golden brown around the edges. Remove from oven, and transfer them to a cooling rack.
Cinnamon Glaze Instructions: In a medium bowl, add all the powder sugar, milk, and cinnamon, then stir until well mixed. If the glaze is stiff, add more milk a little at a time. It should be thick, but run off the spoon.
Pour or spoon the glaze into a piping bag, or a sandwich size ziplock baggie. Make sure glaze is at the tip of the baggie. Tie off the other end with a rubber band, or clip. Then snip a a very small piece of the tip off with scissors, then squeeze to test how much comes out. (Do this in small steps if needed, you don't want to cut too much off, or the glaze will run out.)
Once cooled, place the rack with hand pies over parchment paper and drizzle the glaze over the pies in a back and fourth motion go across them. Let them dry, and the glaze will become firm. Once they're dry, they will be ready to eat!!