Coat the bottoms and sides of a 24-cup mini muffin tin with cooking spray and heat the oven to 350°F. An even coating inside each cavity helps the baked cookie edges release.

Separate the dough into 24 equal squares, using the perforations when present, and place one portion in every cavity. The pieces should look similar in size so the cups bake evenly.

Bake for 18 to 20 minutes, then immediately indent each hot cookie with the rounded handle of a spoon or spatula. Look for light golden edges and press gently while the centers remain pliable, leaving an intact cookie bottom.

Spoon roughly 2 teaspoons of cherry fruit filling into each indentation and set the pan aside. Keep the cherries inside the wells with the cookie rims still visible.

Stir the powdered sugar, almond extract, and heavy whipping cream together until smooth, then drizzle the icing over the filled cups. The icing should fall from the spoon in a smooth ribbon without dry lumps.