Make homemade pie crust dough according to directions. Divide in half, then shape each half into a disc, wrap in plastic wrap, then refrigerate for 30 minutes.
*You can also make the pie dough the night before. Set cold dough on the counter for about 20 minutes the next morning before rolling out.
Make Apple Filling
Peel, core, and dice apples. Place apples into a medium skillet with butter.
In a small bowl whisk together sugar, cinnamon, nutmeg and cloves. Sprinkle over the apples in the saucepan.
Bring to medium low heat until simmering. Stir apples gently with a rubber spatula for 4-5 minutes until the apples are mostly soft. Remove from heat and allow to cool completely.
Assemble Pop Tarts
Remove one disc of pie doughs from the fridge. Place onto a lightly floured works surface. Using a lightly floured rolling pin, carefully roll the dough out into a 10x13 inch rectangle.
Using a ruler and a pastry cutter or sharp knife, cut the dough into a 9x12 inch rectangle. Next, cut the rectangle into 9 equal pieces, each measuring each 3x4 inches.
Place the 9 rectangles on a large parchment paper lined baking tray. Place the tray in the fridge to keep dough cold. Repeat rolling and cutting with second half of dough.
Once all of the dough is cut, preheat the oven to 350 F (180 C) .
Remove the baking sheet from the fridge. Brush the tops of each of the 9 pop tart bases with lightly with egg wash (this will help the top dough to stick to the base and seal in the filling).
Stir the flour and brown sugar together in a small bowl. Sprinkle across the egg wash. Then, spoon a rounded tablespoon of of the apple pie filling onto the center of each pop tart base. Level slightly into a rectangular shape, staying in the center and not pushing towards the edges.
Place the tops onto the each filling covered pop tart base. Use the tines of a fork, to press around the borders of the pop tarts to press the top dough into the base. This will create line indentations around the entire pop tart. Then, gently poke a few air holes across the center of top layer.
Place the tray of pop tarts in the fridge to chill the dough for 25 minutes. Remove tray from fridge, brush a thin coat of egg wash across the tops of the pop tarts. Bake for 25-28 minutes, until lightly golden on edges and tops. Place pan on cooling rack for 5 minutes. Then, transfer pop tarts directly to wire rack to completely cool.
Cinnamon Vanilla Frosting
Once the pop tarts are cooled, you can add the frosting/glaze! Whisk together the powdered sugar, milk, cinnamon, and vanilla in a small bowl until smooth. Add 1/4 cup of powdered sugar for thicker frosting and a teaspoon at a time of milk for thinner. Spoon the frosting onto the tops of the pop tarts and spread with a small spatula.