Remove pie crust from the refrigerator and let set at room temperature for 20 minutes.
Open the canned pie filling and place in a bowl. Using a potato masher, slightly mash the fruit. If you miss this step, the chunks of fruit will be too large and heavy. One can of pie filling makes many batches of this recipe, so you will have leftover filling.
Unroll the pie crusts. Using a 2 1/2 inch cookie or biscuit cutter, cut 10-12 mini pie crusts and place them on a parchment paper lined baking sheet. Cut the same amount of mini pie crusts from the second roll of dough and set aside until ready to use. The size of cutter will determine if you get more than 10-12. Don't make the mistake of using a larger cookie cutter as it will be too heavy to stay upright on the lollipop stick. If children are helping, limit six cut outs on the baking sheet to give space for step 5.
Starting with the pie dough cut outs on the baking sheet, place one or two teaspoons of filling in the center of each cut out. Set the leftover filling aside. Place one lollipop stick on each cutout. I find it easier for children to place the stick on the filling then gently press down. Try to place the stick in the center. If the stick is too close to the bottom edge, it will not support the pie pop.
Place the remaining cut outs on top of the filling. Using a fork, press edges firmly to seal. Be sure to press firmly around the lollipop stick.
Brush beaten egg on each pie pop and sprinkle sugar to taste.