Step 1

Microwave cherry preserves in bowl until fluid, 45 to 60 seconds, stirring halfway through microwaving. Strain preserves through fine-mesh strainer set over bowl, pressing on solids to extract as much liquid as possible; reserve solids (you should have about ⅓ cup) and liquid separately. Set aside to cool.

Step 2

Roll dough into 15-inch circle on floured counter. Using 3-inch round biscuit or cookie cutter, cut 16 rounds from dough circle and transfer to parchment paper–lined rimmed baking sheet. Reserve dough scraps for another use. Cover rounds loosely with plastic wrap and refrigerate until firm but still pliable, about 10 minutes.

Step 3

Line second rimmed baking sheet with parchment. Transfer 8 dough rounds to second prepared sheet, spaced evenly apart. Working with 1 dough round at a time, lay lollipop stick flat on top of dough with 1 end in center of dough round. Press stick firmly into dough. Mound 2 teaspoons cherry solids and 1 teaspoon chocolate chips in center of each dough on top of stick. Transfer sheet with filled rounds to freezer and chill for 10 minutes.

Step 4

Adjust oven rack to upper-middle position and heat oven to 375 degrees. Brush edges of filled dough rounds with egg wash, then top with remaining chilled dough rounds, pressing edges firmly to seal. Crimp edges of each pie with fork. Cut three ½-inch slits in top of each pie and brush with remaining egg wash. Bake until crusts are golden brown, 22 to 26 minutes, rotating sheet halfway through baking. Transfer sheet to wire rack and let pies cool for 10 minutes. Using spatula, carefully transfer pies to wire rack and let cool completely, about 1 hour.

Step 5

Whisk 2 tablespoons reserved cherry preserve liquid and confectioners' sugar together in small bowl until smooth. Let glaze sit until slightly thickened but still able to be drizzled, about 10 minutes. Adjust thickness with up to 1 teaspoon extra cherry liquid as needed. Drizzle pies with glaze and let sit for 10 minutes. Serve.